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

HRID 1110409Notes

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 slurry of 1.4 grams (0.0375 mole) of 95% lithium aluminum hydride in 50 mL of 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 diethyl ether. Upon completion of addition the reaction mixture was heated at reflux for one hour. The reaction mixture was then 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 sequentially 1.4 mL of aqueous 15% sodium hydroxide and 4.2 mL of water were added. The reaction mixture was filtered through diatomaceous earth, and the filtrate was concentrated under reduced pressure yielding 19.5 grams of 4-fluoro-3-phenoxyphenylmethanol.

Workup

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

Sources & evidence

ORD record: ord-67d6d2a961534789b40f8106b49b3c8b
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04975451

Reaction notes

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