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

HRID 131293

Reaction equation

HRID 131293 reaction equation
[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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalyst2×HCID 887MethanolSolvent

Procedure

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]+

Workup

  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)

Sources & evidence

ORD record
ord-e57d3a1d53e74c51b6c551c135c5ef87
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Linked notes

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