Iodine → Benzhydrol

HRID 2375137Notes

Reaction equation

HRID 2375137 reaction equation
[CH2:1]([O:8]C1C=CC=CC=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].II.C([C:23]1[CH:30]=[CH:29][C:26](C=O)=[CH:25][CH:24]=1)C(C)C>O1CCCC1>[C:23]1([CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[OH:8])[CH:30]=[CH:29][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 807IodineHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 577537Benzaldehyde, 4-(2-methylpropyl)-HCID 5462224Magnesium

Product 1

HCID 7037BenzhydrolYield 164.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A Grignard reagent was prepared from 2-benzyloxy-bromobenzene (0.20 g), magnesium (0.026 g), a catalytic amount of iodine and tetrahydrofuran (1 mL). The obtained Grignard reagent was added to a solution of 4-isobutylbenzaldehyde (0.16 g) in tetrahydrofuran (2 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran) to give a diphenylmethanol compound (0.23 g). The obtained diphenylmethanol compound was dissolved in ethanol (3 mL) and concentrated hydrochloric acid (0.1 mL). To the solution was added a catalytic amount of 10% palladium-carbon powder, and the mixture was stirred under a hydrogen atmosphere at room temperature overnight. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/hexane=1/1) to give 2-(4-isobutylbenzyl)phenol (0.10 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: tetrahydrofuran)

Sources & evidence

ORD record
ord-0e73da03a36a409b834792aedaa74799
Source dataset
uspto-grants-2008_12
Patent number
US07465712B2

Reaction notes

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