Methanol → (2E)-2-(4-Bromophenyl)-3-cyclohexylprop-2-en-1-ol

HRID 2103633Notes

Reaction equation

CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[CH:16]=[CH:15][C:14](/[C:17](=[CH:21]\[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)/[C:18](O)=[O:19])=[CH:13][CH:12]=1.CO>C1(C)C=CC=CC=1>[Br:10][C:11]1[CH:12]=[CH:13][C:14](/[C:17](=[CH:21]\[CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)/[CH2:18][OH:19])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Add DIBAL in toluene (673 mL, 1.0 M, 673 mmol) to a solution of (E)-2-(4-bromo-phenyl)-3-cyclohexyl-acrylic acid (52 g, 168 mmol) in toluene (1.6 1) maintained at −78° C. Then allow the reaction mixture to slowly warm to room temperature, and stir, it for 18 h. Cool reaction mixture to 0° C. and add MeOH to destroy excess amounts of DIBAL. Add Rochelle's salt (100 mL) and HCl (2 N). Separate the layers and wash the organic layer with brine. Filter through hydrophobic filter and concentrate to obtain the title compound (48.8 g) as a white solid. MS (m/e): 277 (M+H−H2O).

Workup

temperatureto slowly warm to room temperature
temperatureCool
customreaction mixture to 0° C.
customto destroy excess amounts of DIBAL
customSeparate the layers
washwash the organic layer with brine
filtrationFilter
filtrationthrough hydrophobic filter
concentrationconcentrate

Sources & evidence

ORD record: ord-bdacf65e8f8b43818d7fe337e73943f3
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576108B2

Reaction notes

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