1-(4-Benzyloxy-phenyl)-3,3-dimethyl-cyclohexanol → 1-Benzyloxy-4-(3,3-dimethyl-cyclohex-1-enyl)-benzene

HRID 237759Notes

Reaction equation

HRID 237759 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[CH2:20][CH2:19][CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCO.Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH2:20][CH2:19][CH2:18][C:17]([CH3:22])([CH3:21])[CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 685239591-(4-Benzyloxy-phenyl)-3,3-dimethyl-cyclohexanol

Product 1

HCID 685247081-Benzyloxy-4-(3,3-dimethyl-cyclohex-1-enyl)-benzeneYield 92.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

1-(4-Benzyloxy-phenyl)-3,3-dimethyl-cyclohexanol (5.08 g, 16.4 mmol) was dissolved in EtOH (80 mL) after which concentrated hydrochloric acid (8 mL) was added. This mixture was stirred at 50° C. for 1.5 hours. The solvent was removed under reduced pressure. Water (15 mL) was added. The mixture was basified with aqueous ammonia and extracted three times with EtOAc. The organic phase was dried and concentrated to provide the title compound as a yellow solid 4.43 g as a mixture of isomers.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. additionWater (15 mL) was added
  4. extractionextracted three times with EtOAc
  5. customThe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0abd5aa8aad74627a470f8b01f77990a
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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