Water → 2-[2-(Hydroxymethyl)phenyl]ethanol

HRID 1503366Notes

Reaction equation

HRID 1503366 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8])(O)=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[OH:8][CH2:7][C:6]1[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=1[CH2:4][CH2:1][OH:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 66643Homophthalic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2390242-[2-(Hydroxymethyl)phenyl]ethanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(carboxymethyl)benzoic acid (9 g, 0.05 mol) in THF (200 mL) was added to LAH in THF (250 mL) dropwise, the mixture was refluxed for 18 hours. The mixture was cooled in ice bath and carefully added water dropwise, followed by 50% NaOH (150 mL), then removed the ice bath and added water slowly with stirring until the gray precipitate turns white. The mixture was filtrated and the filtrate was concentrated to give crude 2-(2-(hydroxymethyl)phenyl)ethanol (6 g, 80%).

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. temperatureThe mixture was cooled in ice bath
  3. customremoved the ice bath
  4. additionadded water slowly
  5. filtrationThe mixture was filtrated
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-63c4ab50fa27415c9727c81a68b633da
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

Loading…