Perillyl acetate → p-Menthene-7,8-diol

HRID 1604760

Reaction equation

[CH3:1][C:2]([C@@H:4]1[CH2:9][CH:8]=[C:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)=[CH2:3].CC(C1CC=C(C[O:22]C(C)=O)CC1)=C.CC1(C)C2CC1CCC12OC1>>[CH:7]1([CH2:10][OH:11])[CH2:6][CH:5]=[C:4]([C:2]([OH:22])([CH3:1])[CH3:3])[CH2:9][CH2:8]1

Participants

Reactant 3

HCID 61780Perillyl acetate

HCID 930462,10-Epoxypinane2×

HCID 369312Perilla alcohol2×

Product 1

HCID 54428759p-Menthene-7,8-diol

Procedure

The applicant's first preferred method of preparing perillyl alcohol from pure beta pinene oxide is to react pure beta pinene oxide with anhydrous sodium acetate and glacial acetic acid to produce p-menth-1-en-8-acetoxy-7-ol (C), after which the p-menth-1-en-8-acetoxy-7-ol is pyrolyzed to perillyl alcohol in a yield of approximately fifty percent (50%). This represents a facile two step procedure using inexpensive, safe reagents. The applicant's second preferred method of producing perillyl acetate and perillyl alcohol from pure beta pinene oxide is to react pure beta pinene oxide with an acid resin to produce p-menthene-7,8-diol (D) that is then acetylated to afford 7-acetoxy-p-menth-1-en-8-ol (E) which is then dehydrated by any of five different procedures to yield perillyl acetate that can be hydrolyzed to perillyl alcohol.

Sources & evidence

ORD record: ord-33519a9634d54f82945f0e0cd70a9489
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994598

Linked notes

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