Methanol → Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carboxylate

HRID 742797Notes

Reaction equation

HRID 742797 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH3:23]O>>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([O:13][CH3:23])=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 153808804'-(Hydroxymethyl)-[1,1'-Biphenyl]-2-Carboxylic Acid

Product 1

HCID 15380881Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carboxylateYield 89%

Procedure

4.0 g (17.5 mmol) of 2-(4'-hydroxymethylphenyl)benzoic acid was dissolved in methanol (50 ml). Sulfuric acid (1 ml) was added thereto, followed by heating under reflux for 8 hours. After conducting vacuum concentration, water was added thereto, followed by the extraction with chloroform. After the organic phase was washed with water and dried, it was subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 3.8 g of the title compound as an oil (yield 89%). 1H-NMR(400 MHz, CDCl3); δ(ppm) 1.60(1H, br-s), 3.64(3H, s), 4.72(2H, s), 7.29(2H, d, J=8.0 Hz), 7.33(1H, dd, J=7.7, 1.4 Hz), 7.38(1H, td, J=7.7, 1.4 Hz), 7.39(2H, d, J=8.0 Hz), 7.51(1H, td, J=7.7, 1.4 Hz), 7.81(1H, dd, J=7.7, 1.4 Hz)

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 8 hours
  3. concentrationvacuum concentration, water
  4. additionwas added
  5. extractionfollowed by the extraction with chloroform
  6. washAfter the organic phase was washed with water
  7. customdried
  8. concentrationit was subjected to vacuum concentration
  9. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-3ad6a8185cb847fba8d7bbd7f251c9d7
Source dataset
uspto-grants-1996_09
Patent number
US05554757

Reaction notes

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