Water → 3-(4-Fluorophenyl)propan-1-ol

HRID 1156849Notes

Reaction equation

HRID 1156849 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 1363023-(4-Fluorophenyl)propionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 137472413-(4-Fluorophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 43.6 g of 3-(4-fluorophenyl)propionic acid in 300 ml of tetrahydrofuran is added dropwise to a suspension of 19.7 g of lithium aluminum hydride in 300 ml of tetrahydrofuran at a reaction temperature of about 45° C., while stirring. When the addition has ended, the above temperature is maintained for a further 2.5 hours and 80 ml of water and 20 ml of 4 N sodium hydroxide solution are then successively added dropwise. The precipitate is filtered off and rinsed several times with diethyl ether and the combined solutions are dried over sodium sulfate and concentrated. 39.7 g of 3-(4-fluorophenyl)propan-1-ol remain as an almost colorless oil.

Workup

  1. additionWhen the addition
  2. temperaturethe above temperature is maintained for a further 2.5 hours
  3. filtrationThe precipitate is filtered off
  4. washrinsed several times with diethyl ether
  5. dry with materialthe combined solutions are dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fda0f287bbaa472b9fd0899022d3857d
Source dataset
uspto-grants-1982_06
Patent number
US04337267

Reaction notes

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