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

HRID 1082019Notes

Reaction equation

HRID 1082019 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%).

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-b622edb1de59499f82afcecc6a3f275f
Source dataset
uspto-grants-1996_12
Patent number
US05587504

Reaction notes

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