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PROCESS FOR PREPARING 2-(1,5,5-TRIMETHYL-2-CYCLOPENTENYL)ETHYL ACETATE

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  • Publication Date:
    January 5, 2023
  • معلومة اضافية
    • Document Number:
      20230002307
    • Appl. No:
      17/805520
    • Application Filed:
      June 06, 2022
    • نبذة مختصرة :
      The present invention provides a process for preparing 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising: subjecting a haloacetaldehyde alkyl 3,4,4-trimethyl-2-cyclopentenyl acetal compound of the following general formula (1), wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,5,5-trimethyl-2-cyclopentenyl)acetate compound of the following general formula (2), wherein R is as defined above, and subjecting the alkoxycarbonylmethyl group (i.e., —CH2C(═O)OR) of the (1,5,5-trimethyl-2-cyclopentenyl)acetate compound (2) to a multi-step conversion to be converted into a 2-acetoxyethyl group (i.e., —CH2CH2OAc) to obtain 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate (3). [chemical expression included]
    • Claim:
      1. A process for preparing 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate (3) of the following formula (3): [chemical expression included] wherein Ac represents an acetyl group, the process comprising: subjecting a haloacetaldehyde alkyl 3,4,4-trimethyl-2-cyclopentenyl acetal compound of the following general formula (1): [chemical expression included] wherein R represents a linear or branched alkyl group having 1 to 4 carbon atoms, and Y represents a halogen atom, to a dehydrohalogenation reaction in the presence of a base, followed by a rearrangement reaction to obtain a (1,5,5-trimethyl-2-cyclopentenyl)acetate compound of the following general formula (2): [chemical expression included] wherein R is as defined above, and subjecting the alkoxycarbonylmethyl group (i.e., —CH2C(═O)OR) of the (1,5,5-trimethyl-2-cyclopentenyl)acetate compound (2) to a multi-step conversion to be converted into a 2-acetoxyethyl group (i.e., —CH2CH2OAc) to obtain 2-(1,5,5-trimethyl-2-cyclopentenyl)ethyl acetate (3).
    • Claim:
      2. The process according to claim 1, wherein the multi-step conversion comprises a reduction reaction, followed by an acetylation reaction.
    • Claim:
      3. The process according to claim 1, wherein the multi-step conversion comprises a hydrolysis reaction, followed by a reduction reaction, and then an acetylation reaction.
    • Current International Class:
      07
    • الرقم المعرف:
      edspap.20230002307