4-Phenoxybenzaldehyde → (4-Phenoxyphenyl)methanol

HRID 1957335Notes

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 H2O, 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. 1H NMR (300 MHz, CDCl3) δ1.68 (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 H2O, 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-b428dc93b9f84669a5fd88ef51209104
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783593

Reaction notes

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