methyl 4-(4-hydroxy-1-butynyl)phenylacetate → methyl 4-(4-hydroxybutyl)phenylacetate

HRID 987882Notes

Reaction equation

HRID 987882 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1>CO.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 10536788methyl 4-(4-hydroxy-1-butynyl)phenylacetate

Product 1

HCID 10262968methyl 4-(4-hydroxybutyl)phenylacetateYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Methyl 4-(4-hydroxy-1-butynyl)phenylacetate (10.6 g, 0.0485 mol) was dissolved in methanol (200 mL), then 10% palladium on carbon (1.1 g) was added, and the mixture was stirred under hydrogen (50 psi). After 6 hours, additonal 10% palladium on carbon (1 g) was added, and the mixture was stirred overnight. The catalyst was filtered through celite, the filtrate was concentrated and dried in vacuo to give 10.20 g (94.5%) of methyl 4-(4-hydroxy-1-butyl)phenylacetate as a yellow liquid. FAB-MS m/z=223 (M+H); HRMS calcd for C13H19O3 (M+H) 223.1334, found 223.1328.

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationThe catalyst was filtered through celite
  3. concentrationthe filtrate was concentrated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-12df086610bb43068395a62be9714e57
Source dataset
uspto-grants-2003_10
Patent number
US06632921B1

Reaction notes

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