4-Phenethyloxybenzoic Acid Methyl Ester → (4-Phenethyloxyphenyl)methanol

HRID 970787Notes

Reaction equation

HRID 970787 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[CH2:11]([O:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 120638344-Phenethyloxybenzoic Acid Methyl EsterHCID 21226445Aluminium lithium hydride

Product 1

HCID 12990905(4-Phenethyloxyphenyl)methanolYield 98.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

4-Phenethyloxybenzoic acid methyl ester 10 (7.66 g, 29.89 mmol) was dissolved in diethyl ether and chilled to 0° C. LiAlH4 was slowly added and allowed to stir at 0° C. for 3 hours. The mixture was quenched with H2O. After addition of 3N NaOH the mixture was allowed to stir for 30 min. The mixture was then acidified with 4.5N HCl, extracted, dried, and concentrated in vacuo to give about 6.7 g of a crystalline (4-phenethyloxyphenyl)methanol 11.

Workup

  1. customThe mixture was quenched with H2O
  2. additionAfter addition of 3N NaOH the mixture
  3. stirringto stir for 30 min
  4. extractionextracted
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b73287181d294dbcbbad791e91949adc
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

Loading…