Sodium Hydroxide → 4-hydroxy-3-(4-methoxyphenyl)benzyl Alcohol

HRID 460129Notes

Reaction equation

HRID 460129 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6](OCC)=[O:7])=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.OC1C=CC(C(O)=O)=CC=1C1C=CC(OC)=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 223911504-Hydroxy-3-(4-methoxyphenyl)benzoic acidHCID 22391340HCID 22391340, compound

Product 1

HCID 688406354-hydroxy-3-(4-methoxyphenyl)benzyl Alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Ethyl 4-hydroxy-3-(4-methoxyphenyl)benzoate and 4-hydroxy-3-(4-methoxyphenyl)benzoic acid (5.3 g, 19.47 mmol) in anhydrous THF (100 mL) was cooled to 0° C. and treated with LiAlH4 (2.95 g, 77.8 mmol); the mixture was then heated at 65 C for one hour then cooled and aqueous NaOH (5%, 19.4 mL) was added drop wise. The resulting precipitate was filtered off and the filtrate concentrated under reduced pressure to afford 5.54 g of crude product.

Workup

  1. temperaturethe mixture was then heated at 65 C for one hour
  2. temperaturethen cooled
  3. filtrationThe resulting precipitate was filtered off
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-917850fa9972446588ae25f4a876e925
Source dataset
uspto-grants-2007_03
Patent number
US07196102B2

Reaction notes

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