Carvacrol → 3-Cyclohexene-1-ethanol, 4-methyl-.beta.-methylene-

HRID 2308172Notes

Reaction equation

HRID 2308172 reaction equation
[OH-:1].[Ca+2].[OH-].[CH:4]1[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][CH:9]=[C:7]([CH3:8])[C:5]=1O>>[C:7]1([CH3:8])[CH2:9][CH2:10][CH:11]([C:12]([CH2:14][OH:1])=[CH2:13])[CH2:4][CH:5]=1

Participants

3

Reactant 2

HCID 10364CarvacrolHCID 6093208Calcium Hydroxide

Product 1

HCID 5271433-Cyclohexene-1-ethanol, 4-methyl-.beta.-methylene-

Conditions

Temperature
222.5 °C

Procedure

A mixture of 300 parts of 8,9-limonene oxide, 6 parts of calcium hydroxide and 6 parts of carvacrol was refluxed at 215-230° C. for 2 hours in a three-necked flask equipped agitator, Dean-Stark trap, and temperature probe. After cooling and filtration 290 parts of the mixture containing 30% of unreacted epoxide and 43% 1,8-p-menthadien-10-ol (61% selectivity) was obtained.

Workup

  1. customequipped agitator, Dean-Stark trap, and temperature probe
  2. temperatureAfter cooling
  3. filtrationfiltration 290 parts of the mixture
  4. additioncontaining 30% of unreacted epoxide

Sources & evidence

ORD record
ord-b36d7b430de54f25a91876623809740b
Source dataset
uspto-grants-2004_12
Patent number
US06835686B2

Reaction notes

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