p-Toluenesulfonic acid → [4-(4-Benzyloxy-phenyl)-5-ethyl-6-methyl-cyclohex-3-enyl]-methanol

HRID 351440Notes

Reaction equation

HRID 351440 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[CH2:20][CH2:19][CH:18]([CH2:21][OH:22])[CH:17]([CH3:23])[CH:16]2[CH2:24][CH3:25])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]([CH2:24][CH3:25])[CH:17]([CH3:23])[CH:18]([CH2:21][OH:22])[CH2:19][CH:20]=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 6101p-Toluenesulfonic acidHCID 184363251-(4-Benzyloxy-phenyl)-2-ethyl-4-hydroxymethyl-3-methyl-cyclohexanol

Product 1

HCID 18436344[4-(4-Benzyloxy-phenyl)-5-ethyl-6-methyl-cyclohex-3-enyl]-methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1-(4-benzyloxy-phenyl )-2-ethyl-4-hydroxymethyl-3-methyl-cyclohexanol (7.8 g, 0.0166 mol) was added pTSA (1.8 g, 1 eq.) in DCM (100 mL). The reaction mixture was refluxed for 8 h. DCM (200 mL) was added and the mixture was washed with aqueous saturated NaHCO3 (3×300 mL). The organic layer was separated, dried over MgSO4 and purified on SiO2 (50% ethyl acetate/hexane) twice to yield [4-(4-benzyloxy-phenyl)-5-ethyl-6-methyl-cyclohex-3-enyl]-methanol.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. washthe mixture was washed with aqueous saturated NaHCO3 (3×300 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. custompurified on SiO2 (50% ethyl acetate/hexane) twice

Sources & evidence

ORD record
ord-649347afd0df46a1966f1692baaf0e88
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Reaction notes

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