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US4162256A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the production of compounds useful in perfumery

Assignee: International Flavors and Fragrances Inc
•
Filing: 1978-04-19
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Granted: 1979-07-24
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Expires: 1998-04-19
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Abstract

Abstract Process for producing compounds useful in perfumery including isochromans and acylated indane hydrocarbons with an alkylene oxide or with a lower acyl halide in the presence of a hydrocarbon or hydrocarbon mixture containing C 5 to C 10 alkanes at a temperature of from -20° C. up to -5° C. In the case of forming isochromans, the resulting alcohol is reacted, in situ, with a lower alkanol and a formaldehyde precursor at temperatures of from 20° C. up to 80° C.

Inventors

  • 👤 Mark A. Sprecker
  • 👤 Ernst T. Theimer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 04:52
CPC Classifications
C; C11; C11B; C11B9/00; C11B9/0069; C11B9/0073; C11B9/008; C07; C07C; C07C29/00; C07C29/36; C07C45/00; C07C45/45; C07C45/46; C07C49/00; C07C49/76; C07C49/782; C07C49/792; C07D; C07D311/00; C07D311/02; C07D311/78; C07D311/92; C07D311/94; C07C2602/00; C07C2602/02; C07C2602/04; C07C2602/08; C07C2602/10

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 224 words
A process for preparing an isochroman derivative having a structure selected from the group consisting of ##STR25## comprising the steps of reacting a hydrocarbon reactant which is an indane or tetrahydronaphthalene derivative having a structure selected the group consisting of: ##STR26## with propylene oxide in the presence of a solvent consisting essentially of at least one aliphatic saturated C 5 -C 10 hydrocarbon, said, aliphatic saturated hydrocarbon being halogen-free, at a temperature between -20° C. and -5° C. in the presence of an aluminum chloride catalyst; the weight ratio of the aliphatic saturated hydrocarbon to the indane or tetrahydronaphthalene derivative being from 1:10 up to 10:1; the mole ratio of aluminum chloride to propylene oxide being from 1:1 up to 2:1; the mole ratio of indane or tetrahydronaphthalene derivative to propylene oxide being from 1:1 up to 10:1; followed by addition of a lower C 1 -C 6 alkanol at a temperature of -20° C. to 0° C.; the mole ratio of aluminum chloride to C 1 -C 6 alkanol being from 2:1 up to 1:2; followed by addition at a temperature of from 20° C. up to 80° C. of a formaldehyde equivalent having the structure: R'.sub.11 --O--CH.sub.2 --O--R'.sub.11 wherein R' 11 represents C 1 to C 6 alkyl, or paraformaldehyde; and then quenching the resulting reaction mass by pouring it into water.
Claim 2
Dependent Claim 224 words
A process for preparing an isochroman derivative having a structure selected from the group consisting of ##STR25## comprising the steps of reacting a hydrocarbon reactant which is an indane or tetrahydronaphthalene derivative having a structure selected the group consisting of: ##STR26## with propylene oxide in the presence of a solvent consisting essentially of at least one aliphatic saturated C 5 -C 10 hydrocarbon, said, aliphatic saturated hydrocarbon being halogen-free, at a temperature between -20° C. and -5° C. in the presence of an aluminum chloride catalyst; the weight ratio of the aliphatic saturated hydrocarbon to the indane or tetrahydronaphthalene derivative being from 1:10 up to 10:1; the mole ratio of aluminum chloride to propylene oxide being from 1:1 up to 2:1; the mole ratio of indane or tetrahydronaphthalene derivative to propylene oxide being from 1:1 up to 10:1; followed by addition of a lower C 1 -C 6 alkanol at a temperature of -20° C. to 0° C.; the mole ratio of aluminum chloride to C 1 -C 6 alkanol being from 2:1 up to 1:2; followed by addition at a temperature of from 20° C. up to 80° C. of a formaldehyde equivalent having the structure: R'.sub.11 --O--CH.sub.2 --O--R'.sub.11 wherein R' 11 represents C 1 to C 6 alkyl, or paraformaldehyde; and then quenching the resulting reaction mass by pouring it into water.
Claim 3
Dependent Claim 25 words
The process of claim 1 wherein the isochroman derivative prepared has the structure: ##STR27## and the hydrocarbon reactant is a tetrahydronaphthalene having the structure: ##STR28##
Claim 4
Dependent Claim 22 words
The process of claim 1 wherein the isochroman derivative produced has the structure: ##STR29## and the hydrocarbon reactant has the structure: ##STR30##
Claim 5
Dependent Claim 20 words
The process of claim 1 wherein the solvent used is selected from the group consisting of 2,2,4-trimethylpentane, n-hexane and n-octane.
Claim 6
Dependent Claim 11 words
The process of claim 4 wherein the solvent used is 2,2,4-trimethylpentane.
Claim 7
Dependent Claim 41 words
The process of claim 1 wherein the weight ratio of aliphatic saturated C 5 -C 10 alkane hydrocarbon solvent: hydrocarbon reactant is from 0.2:1 up to 0.3:1 and the mole ratio of aluminum chloride:propylene oxide varies from 1:1 up to 1.02:1.
Claim 8
Dependent Claim 21 words
The process of claim 1 wherein the formaldehyde equivalent is selected from the group consisting of parformaldehyde, di-isopropylformal and di-methoxy methane.

References Cited (Backward Citations)

US3360530A Cited
US3532719A Cited
US3910964A Cited
US4066648A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-07-23 1983-01-22 1983-07-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-07-23 1987-01-22 1987-07-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-07-23 1991-01-22 1991-07-24 $7700.00 Window Closed / Lapsed

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