Acetic Acid → Perilla alcohol

HRID 1076331

Reaction equation

[CH3:1][C:2]1([CH3:10])[CH:8]2[CH2:9][CH:3]1[CH2:4][CH2:5][C:6]2=[CH2:7].C(O)(=[O:13])C>>[CH3:1][C:2]([C@@H:3]1[CH2:9][CH:8]=[C:6]([CH2:7][OH:13])[CH2:5][CH2:4]1)=[CH2:10]

Participants

Reactant 2

HCID 176Acetic Acid

HCID 14896Beta-Pinene

Product 1

HCID 369312Perilla alcoholYield 40%

Procedure

The solvent system must be polar. If the non-polar beta-pinene is used in excess as the solvent, the reaction products are only polymeric substances. For reasons not apparent, if the solvent is glacial acetic acid alone, a completely polar solvent system, perillyl alcohol is obtained in only about a 40% yield.

Sources & evidence

ORD record: ord-38df2237c93f41cb9b9ab887957e39da
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03956404

Linked notes

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