Methyl 4-(3-hydroxyprop-1-ynyl)benzoate → Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl ester

HRID 131293

反応式

HRID 131293 の反応式
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1>CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[OH:1][CH2:2][CH:3]=[CH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1

参加物

4

反応物 1

HCID 4448596Methyl 4-(3-hydroxyprop-1-ynyl)benzoate

生成物 1

HCID 54205360Benzoic acid, 4-(3-hydroxy-1-propen-1-yl)-, methyl ester収率 75%

試薬・触媒・溶媒 2

HCID 131709914Lindlars catalyst触媒2 回HCID 887Methanol溶媒

実験手順

To a solution of methyl 4-(3-hydroxy-1-propinyl)benzoate (2 g) in methanol (32 mL) is added Lindlar catalyst (238 mg) and the mixture is stirred under hydrogen gas atmosphere at room temperature for 18 hours. To the reaction mixture is added Lindlar catalyst (90 mg) and the mixture is stirred for 1 hour. The reaction mixture is filtered to remove insoluble materials through Celite. The filtrate is concentrated in vacuo and the residue is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=100:0→50:50) to give methyl 4-(3-hydroxy-1-propenyl)-benzoate (1.5 g, yield; 75%) as an amorphous powder. MS (APCI) m/z; 175 [M+H−H2O]+

後処理

  1. stirringthe mixture is stirred for 1 hour
  2. filtrationThe reaction mixture is filtered
  3. customto remove insoluble materials through Celite
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is purified by column chromatography on silica gel (Solvent; n-hexane:ethyl acetate=100:0→50:50)

出典と根拠

ORDレコード
ord-e57d3a1d53e74c51b6c551c135c5ef87
出典データセット
uspto-grants-2008_06
特許番号
US07384952B2

関連ノート

読み込み中…