Water → 1,2-Benzenediethanol

HRID 1503402Notes

Reaction equation

HRID 1503402 reaction equation
[C:1]1([CH2:11][C:12](O)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8](O)=[O:9].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:2]1([CH2:7][CH2:8][OH:9])[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:11][CH2:12][OH:13]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24123o-Phenylenediacetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 2519601,2-BenzenediethanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2,2′-(1,2-phenylene)diacetic acid (10 g, 51.5 mmol) in THF (100 mL) was added to LAH in THF (90 mL) dropwise, the mixture was refluxed for 18 hours. The mixture was cooled in ice bath and carefully added water (8 mL) dropwise, followed by 1 N NaOH (8 mL), then removed the ice bath 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′-(1,2-phenylene)diethanol (8 g, 94%). 1H-NMR (CDCl3): 2.02 (s, 3H), 2.97 (m, 4H), 3.83 (m, 2H), 4.12 (m, 1H), 4.24 (t, 1H), 7.19 (m, 4H).

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-e1b134da8d814afaad6242d7044d3f1d
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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