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

HRID 742797

반응식

HRID 742797 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-3ad6a8185cb847fba8d7bbd7f251c9d7
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05554757

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