Acetic Anhydride → Perilla alcohol

HRID 1604758

Reaction equation

HRID 1604758 reaction equation
[CH3:1][C:2]1([CH3:11])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][C:6]12[O:10][CH2:9]1.C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:11][C:2]([C@@H:3]1[CH2:4][CH:5]=[C:6]([CH2:9][OH:10])[CH2:7][CH2:8]1)=[CH2:1]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 930462,10-Epoxypinane

Product 1

HCID 369312Perilla alcohol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Among other routes that have been developed to prepare perillyl alcohol from beta pinene oxide is that reported by T. K. Keenan in 1966 who produced perillyl acetate from beta-pinene oxide by refluxing beta-pinene oxide with acetic anhydride and acetic acid for seven hours followed by removal of the acetate to afford a nine percent (9%) yield of perillyl alcohol based on the starting beta-pinene oxide (B.S. Thesis Mass. Institute of Tech.). The applicants found the process to be reproducible albeit in low yield. F. C. Delay in Swiss Patent 5671/84 reported the production of perillyl alcohol in which he treated beta-pinene oxide with nitromethane and ammonium nitrite at a temperature between 20° C. and 90° C. in an overall yield of thirty percent (30%). Two years later Wang and co-workers published in Tetrahedron 1986, 620-638 complete details of this procedure and reported an overall yield of sixty-eight percent (68%) perillyl alcohol.

Workup

  1. customfollowed by removal of the acetate

Sources & evidence

ORD record
ord-bfd85e66572b4d889adea2b672358d80
Source dataset
uspto-grants-1999_11
Patent number
US05994598

Linked notes

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