Isophorol → 5,5-Dimethyl-3-methylidenecyclohexene

HRID 25887Notes

Reaction equation

[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][CH:4](O)[CH:3]=1.C(OCC1(O)C=CCC(C)(C)C1)(=O)C>>[CH2:1]=[C:2]1[CH:3]=[CH:4][CH2:5][C:6]([CH3:9])([CH3:8])[CH2:7]1

Participants

Reactant 2

HCID 79016Isophorol

HCID 54032990(1-Hydroxy-3,3-dimethyl-cyclohex-5-en-1-yl)-methyl acetate

Product 1

HCID 133542465,5-Dimethyl-3-methylidenecyclohexene

Procedure

1-Methylene-3,3-dimethyl-cyclohex-5-ene was prepared by the procedure given in Bull. Soc. Chim. France 4170 (1972) starting from isophorol. Its conversion into (1-hydroxy-3,3-dimethyl-cyclohex-5-en-1-yl)-methyl acetate was performed as follows:

Sources & evidence

ORD record: ord-2c3362a3307a47ea9c6544fd41777bc6
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04147672

Reaction notes

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