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

HRID 131293

반응식

HRID 131293 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 131709914Lindlars catalyst촉매2회HCID 887Methanol용매

실험 절차

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]+

후처리

  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)

출처 및 근거

ORD 기록
ord-e57d3a1d53e74c51b6c551c135c5ef87
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384952B2

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