Boron Trichloride → 4-[4-(Hydroxymethyl)-4-methyl-1-cyclohexenyl]phenol

HRID 351432Notes

Reaction equation

HRID 351432 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH2:20][CH2:19][C:18]([CH2:22][OH:23])([CH3:21])[CH2:17][CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl>C(Cl)Cl>[OH:23][CH2:22][C:18]1([CH3:21])[CH2:19][CH2:20][C:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)=[CH:16][CH2:17]1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 18436343[4-(4-Benzyloxy-phenyl)-1-methyl-cyclohex-3-enyl]-methanol

Product 1

HCID 184363464-[4-(Hydroxymethyl)-4-methyl-1-cyclohexenyl]phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of [4-(4-benzyloxy-phenyl)-1-methyl-cyclohex-3-enyl]-methanol (102 mg, 0.331 mmol) in DCM (5.0 mL) at −78° C. was added BCl3 (1.0 M in hexanes, 0.5 mL). The reaction mixture was then stirred at −78° C. for 3 h. The mixture was then quenched with aqueous saturated NaHCO3 (30 mL), extracted with ethyl acetate (60 mL), dried over MgSO4 and purified by SiO2 (50˜70% ethyl acetate/Hexanes) to yield 4-(4-hydroxymethyl-4-methyl-cyclohex-1-enyl)-phenol as a liquid.

Workup

  1. customThe mixture was then quenched with aqueous saturated NaHCO3 (30 mL)
  2. extractionextracted with ethyl acetate (60 mL)
  3. dry with materialdried over MgSO4
  4. custompurified by SiO2 (50˜70% ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-85535bd42ddb48af9e07da3db3ef0143
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Reaction notes

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