Water → 1-(2-(Hydroxymethyl)phenyl)ethanol

HRID 1461758Notes

Reaction equation

HRID 1461758 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13])(=[O:9])[CH3:8].O.[OH-].[Na+]>C(OCC)C.O1CCCC1>[OH:9][CH:7]([C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[CH2:12][OH:13])[CH3:8]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 684742-Acetylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5769111-(2-(Hydroxymethyl)phenyl)ethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 12 g of lithium aluminium hydride in 50 ml of dry diethyl ether was added dropwise with stirring a solution of 25 g (152.4 mM) of 2-acetylbenzoic acid in 120 ml of dry tetrahydrofuran. After heating under reflux for 6 hours, the mixture was cooled and treated carefully with 12 ml of water, 12 ml of 10% sodium hydroxide solution and 24 ml of water. The solution was filtered, the filtrate was dried over magnesium sulphate, filtered and evaporated to yield the title compound as a colourless waxy solid.

Workup

  1. additionwas added dropwise
  2. temperatureAfter heating
  3. temperatureunder reflux for 6 hours
  4. temperaturethe mixture was cooled
  5. filtrationThe solution was filtered
  6. dry with materialthe filtrate was dried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-761ef2f2bd07457c971fbb0c7e0abcf9
Source dataset
uspto-grants-1991_12
Patent number
US05077299

Reaction notes

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