4-Phenoxybenzaldehyde → (4-Phenoxyphenyl)methanol

HRID 1781167Notes

Reaction equation

[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][OH:13])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-phenoxybenzaldehyde (10.0 g, 50 mmol) and 10 mL dry THF was added dropwise to a 0° C. suspension of lithium aluminum hydride (2.1 g, 55.3 mmol) and 100 mL dry THF. The reaction mixture was stirred for 1 hour at 0° C., then was quenched successively with 2.1 mL H20, 2.1 mL 10% NaOH, and 6.3 mL H2O. The resultant slurry was stirred for 1.5 hours at room temperature, then was filtered through Celite® and the filtrate was evaporated under reduced pressure to afford the title compound (9.9 g) as a white solid. 1HNMR (300 MHz, CDCl3) δ 1.68 (t, 1H), 4.68 (d, 2H), 7.00 (m, 4H), 7.10 (t, 1H), 7.35 (m, 4H). MS (DCl/NH3) m/e 183 (M+1, -H2O)+.

Workup

customwas quenched successively with 2.1 mL H20, 2.1 mL 10% NaOH, and 6.3 mL H2O
stirringThe resultant slurry was stirred for 1.5 hours at room temperature
filtrationwas filtered through Celite®
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-738e7cb49cf74664a77d5d70d96138ca
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05631401

Reaction notes

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