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

HRID 472950

Reaction equation

HRID 472950 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-efec38a8c2c74880b1bcd89041d94028
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Linked notes

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