alpha-Pinene oxide → 3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-

HRID 1058209Notes

Reaction equation

HRID 1058209 reaction equation
[CH3:1][C:2]1([CH3:11])[CH:5]2[C:6]3([CH3:10])[O:9][CH:7]3[CH2:8][CH:3]1[CH2:4]2>[Br-].[Zn+2].[Br-].C1C=CC=CC=1>[CH3:4][C:5]1[C:2]([CH3:1])([CH3:11])[CH:3]([CH2:8][CH:7]=[O:9])[CH2:10][CH:6]=1

Participants

4

Reactant 1

HCID 91508alpha-Pinene oxide

Product 1

HCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-Yield 80%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 241BenzeneSolvent

Procedure

According to this article, α-pinene oxide rearranged exothermically in the presence of zinc bromide catalyst in benzene solvent to give about 80% yield of alpha-campholenic aldehyde (Scheme 1). Since then, this batch process, or variations thereof, has been described in numerous publications and patents.

Sources & evidence

ORD record
ord-95fc5f36ceaa4b9d8c4e96a2e3efc6fe
Source dataset
uspto-grants-2003_02
Patent number
US06515186B2

Reaction notes

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