Methyl 4-(2-fluoroethoxy)benzoate → (4-(2-Fluoroethoxy)phenyl)methanol

HRID 1087889Notes

Reaction equation

HRID 1087889 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][CH:6]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[OH:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][F:1])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 10943448Methyl 4-(2-fluoroethoxy)benzoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 13367643(4-(2-Fluoroethoxy)phenyl)methanolYield 83.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 7.0 grams (0.035 mole) of methyl 4-(2-fluoroethoxy)benzoate and 75 ml of a 1.0 M solution of diisobutylaluminium hydride in hexanes in 75 ml of toluene was heated at 40° C. for three hours. The mixture was cooled and quenched with methanol. This mixture was stirred at room temperature for approximately 18 hours and was filtered through a pad of celite. The filter cake was washed with a small amount of methanol. The combined filtrate was evaporated under reduced pressure to yield 5.0 grams of 2-fluoroethyl 4-hydroxymethylphenyl ether as an oil which slowly solidified.

Workup

  1. temperatureThe mixture was cooled
  2. customquenched with methanol
  3. filtrationwas filtered through a pad of celite
  4. washThe filter cake was washed with a small amount of methanol
  5. customThe combined filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b8c27fc0081d4add8231e931a30dfd86
Source dataset
uspto-grants-1990_10
Patent number
US04960884

Reaction notes

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