Hydrochloric Acid → Bis(3-isobutylphenyl)methanol

HRID 249143Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]=1.[Mg].BrCCBr.[CH2:17]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25])[CH:18]([CH3:20])[CH3:19].Cl>O1CCCC1.II.C(OCC)(=O)C>[CH2:17]([C:21]1[CH:22]=[C:23]([CH:24]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]=2)[OH:25])[CH:26]=[CH:27][CH:28]=1)[CH:18]([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 1-bromo-3-isobutylbenzene (3.16 g), magnesium (1.08 g), 1,2-dibromoethane (2.78 g) and iodine (10 mg) in tetrahydrofuran (10 ml) was refluxed for 1.5 hours. The mixture was cooled to 25° C., and a solution of 3-isobutylbenzaldehyde (2.40 g) in tetrahydrofuran (10 ml) was added at 25° C. After stirred for 1 hour at the same temperature, the mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (200 g) eluting with 5% ethyl acetate in hexane to give bis(3-isobutylphenyl)methanol (2.90 g) as a colorless oil.

Workup

temperaturewas refluxed for 1.5 hours
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over magnesium sulfate
customAfter evaporation of the solvent
customthe residue was chromatographed on silica gel (200 g)
washeluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record: ord-ece20f6a2d4d4ebbba9253f0cded847e
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05212320

Reaction notes

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