Water → Benzyl 2,4-dihydroxybenzoate

HRID 129665

反応式

HRID 129665 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O>[OH:3][C:4]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7]

参加物

6

反応物 4

HCID 962WaterHCID 14912,4-Dihydroxybenzoic AcidHCID 7498Benzyl BromideHCID 24758Sodium hydride

生成物 1

HCID 7500968Benzyl 2,4-dihydroxybenzoate収率 81%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 3 g (0.1 mole) of sodium hydride (80% in oil) and 50 ml of dimethylformamide (DMF), there are slowly added 15.4 g (0.1 mole) of 2,4-dihydroxybenzoic acid dissolved in 50 ml of DMF. The mixture is stirred at ambient temperature until the cessation of gaseous emission. There are then added 13.1 ml (0.1 mole) of benzyl bromide and the mixture is stirred at ambient temperature until solubilization of the reaction medium. The reaction mixture is poured into water, and extracted with ethyl ether. The organic phase is decanted, washed with water, dried on magnesium sulfate and evaporated. The residue is purified by chromatography on a silica column by eluting with dichloromethane. 19.7 g (81% yield) of the expected ester having a melting point of 94°-95° C. are recovered.

後処理

  1. stirringthe mixture is stirred at ambient temperature until solubilization of the reaction medium
  2. extractionextracted with ethyl ether
  3. customThe organic phase is decanted
  4. washwashed with water
  5. customdried on magnesium sulfate
  6. customevaporated
  7. customThe residue is purified by chromatography on a silica column
  8. washby eluting with dichloromethane

出典と根拠

ORDレコード
ord-941a7ae7f4d94bd4a18d3bbeba2295c5
出典データセット
uspto-grants-1995_11
特許番号
US05468897

関連ノート

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