(1-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-enyl)-methanol → (1-Methyl-3,4-di(4-hydroxy-phenyl)-cyclohex-3-enyl)-methanol

HRID 351437Notes

Reaction equation

[CH3:1][C:2]1([CH2:36][OH:37])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14]CC3C=CC=CC=3)=[CH:10][CH:9]=2)=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([O:28]CC3C=CC=CC=3)=[CH:24][CH:23]=2)[CH2:3]1>C(Cl)Cl.C(OCC)(=O)C.O.Cl[Ti](Cl)(Cl)Cl>[CH3:1][C:2]1([CH2:36][OH:37])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[C:4]([C:22]2[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=2)[CH2:3]1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of (1-methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-enyl)-methanol (150 mg, 0.306 mmol) in DCM (5.0 mL) at −10° C. was added TiCl4 (0.102 mL, 3.0 eq.) and the reaction mixture stirred at −10° C. for 3 h. The reaction mixture was then diluted with ethyl acetate (20 mL and H2O (10 mL). The organic layer was separated, dried over MgSO4, and purified by SiO2 (50˜100% ethyl acetate/hexane) to yield a lower TLC spot of (1-methyl-3,4-di(4-hydroxy-phenyl)-cyclohex-3-enyl)-methanol.

Workup

customThe organic layer was separated
dry with materialdried over MgSO4
custompurified by SiO2 (50˜100% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-047c0f0bdfd6459eb6cd7bafc05949cb
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183445B2

Reaction notes

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