Ethyl 3-allyl-4-hydroxybenzoate → Ethyl 4-hydroxy-3-propylbenzoate

HRID 2294965Notes

Reaction equation

HRID 2294965 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][CH:13]=[CH2:14])[CH:6]=1)[CH3:2].[H][H]>[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][CH2:13][CH3:14])[CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 12252872Ethyl 3-allyl-4-hydroxybenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 14986319Ethyl 4-hydroxy-3-propylbenzoateYield 115.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl-3-allyl-4-hydroxybenzoate (4.12 g), palladium on carbon (10% w/w) and ethanol (100 ml) was stirred under an atmosphere of hydrogen until 500 ml of hydrogen had been consumed. The mixture was filtered and the filtrate was evaporated. The residue was purified by flash chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent to give ethyl-3-propyl-4-hydroxybenzoate (4.8 g) as a solid, m.p. 78°-79° C.; microanalysis, found: C, 69.2; H, 8.1%; C12H16O3 requires: C, 69.2; H, 7.74%; NMR (CDCl3): 0.97(3H,t), 1.38(3H,t), 1.67(2H,m), 2.60(2H,t), 4.35(2H,q), 5.71(1H,s), 6.79(1H,d) and 7.75-7.87(2H,m); m/z 209(M+H).

Workup

  1. customhad been consumed
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by flash chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-95dee93b60f44bc8b17c1c6c1e8f78a8
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

Loading…