Water → (4-Fluoro-3-phenoxyphenyl)methanol

HRID 1383232Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][C:9]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.[OH-].[Na+]>C(OCC)C>[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][C:9]=1[O:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 15 °C

Procedure

To a stirred suspension of 1.4 grams (0.0375 mole) of lithium aluminum hydride in 50 mL of anhydrous diethyl ether was added dropwise during a one hour period a solution of 21.6 grams (0.1 mole) of 4-fluoro-3-phenoxybenzaldehyde in 50 mL of anhydrous diethyl ether. Upon completion of addition, the reaction mixture was heated at reflux for 1.0 hour. The reaction mixture was cooled to 15° C., and 1.4 mL of water was cautiously added dropwise. Upon completion of addition, the reaction mixture was again cooled to 15° C., and 1.4 mL of an aqueous, 15% sodium hydroxide solution was added dropwise, folowed by an additional 4.2 mL of water. The mixture was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure, yielding 19.5 grams of 4-fluoro-3-phenoxyphenylmethanol as an oil.

Workup

additionUpon completion of addition
temperaturethe reaction mixture was heated
temperatureat reflux for 1.0 hour
additionUpon completion of addition
temperaturethe reaction mixture was again cooled to 15° C.
filtrationThe mixture was filtered through diatomaceous earth
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-10062d2a900d45ce8a1195e0933f017a
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04808762

Reaction notes

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