Hydrochloric Acid → HCID 68526321, compound

HRID 237736Notes

Reaction equation

HRID 237736 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[CH2:20][CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH2:20][CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][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 2

HCID 313Hydrochloric AcidHCID 68523971HCID 68523971, compound

Product 1

HCID 68526321HCID 68526321, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

1-(4-Benzyloxyphenyl)-4,4-dimethyl-cyclohexanol (4.14 g, 13.3 mmol) was dissolved in ethanol (80 mL) by stirring after which concentrated hydrochloric acid (8 ml) was added. This stirred mixture was heated to 50° C. for 1.5 hours. The solvent was removed under reduced pressure. The residue was basified with ammonium hydroxide, extracted three times with EtOAc and the organic extracts combined and concentrated to afford 1-benzyloxy-4-(4,4-dimethylcyclohex-1-enyl)-benzene as a white solid (3.98 g, 99%).

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. extractionextracted three times with EtOAc
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-42cb30f6be294e0bac8e64e7ed6f2118
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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