Acetic Acid → Methyl 4-oxo-4-(4-hydroxyphenyl)butanoate

HRID 34329ノート

反応式

HRID 34329 の反応式
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].Br.[C:17](O)(=O)C>O>[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([O:7][CH3:17])=[O:6]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 766134-Methoxy-gamma-oxobenzenebutanoic acid

生成物 1

HCID 13695066Methyl 4-oxo-4-(4-hydroxyphenyl)butanoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of the compound from Step 1 (77.3 g), 48% HBr (310 ml), and acetic acid (620 ml) was heated under reflux for 18 hours. The resulting mixture was cooled to room temperature and poured into 3 liters of water. The resulting solution was extracted with ethyl acetate (3×500 ml). The combined organic layers were washed with water (4×200 ml), dried over Na2SO4, the solvents were removed by evaporation and the residue was dissolved in 10% HCl/methanol (500 ml). After 10 hours at room temperature the volatile components were removed by evaporation in vacuo. The resulting residue was triturated with hexane to yield the title compound, m.p. 115°-116°.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. extractionThe resulting solution was extracted with ethyl acetate (3×500 ml)
  4. washThe combined organic layers were washed with water (4×200 ml)
  5. dry with materialdried over Na2SO4
  6. customthe solvents were removed by evaporation
  7. dissolutionthe residue was dissolved in 10% HCl/methanol (500 ml)
  8. customAfter 10 hours at room temperature the volatile components were removed by evaporation in vacuo
  9. customThe resulting residue was triturated with hexane

出典と根拠

ORDレコード
ord-7b7e5e9edcee410583c9646daf1f50b7
出典データセット
uspto-grants-1988_08
特許番号
US04761425

反応ノート

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