Water → (4-Fluoro-3-phenoxyphenyl)methanol
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
A suspension of 1.4 grams (0.038 mole) of lithium aluminum hydride in 50 ml of anhydrous diethyl ether was stirred, and a solution of 21.6 grams (0.1 mole) of commercially available 4-fluoro-3-phenoxybenzaldehyde in 50 ml of anhydrous diethyl ether was added dropwise during a one hour period. 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. This was followed by the addition of 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-6ee012f5ee024e768c5ff83573eea833
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05223536
Reaction notes
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