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

HRID 742797

反応式

HRID 742797 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-3ad6a8185cb847fba8d7bbd7f251c9d7
出典データセット
uspto-grants-1996_09
特許番号
US05554757

関連ノート

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