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

HRID 744183Notes

Reaction equation

HRID 744183 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[OH:14])[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3]>CO.[Pd]>[OH:14][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 939882Methyl 3-allyl-4-hydroxybenzoate

Product 1

HCID 11805593Methyl 4-hydroxy-3-propylbenzoateYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 363 g of methyl 3-allyl-4-hydroxybenzoate in 1.5 L of methanol was hydrogenated for 1 hr in a Parr® type shaker at 40 psi and ambient temperature using 1.5 g of 10% palladium on carbon as the catalyst. The reaction was filterd through Solka-Floc® and the cake washed with 1 L of methanol. The combined filtrate was concentrated and the oil flushed with ether. Hexanes (1.5 L) were added and the resulting suspension cooled to 0° C. The product was collected by filtration, washed with hexanes and dried affording 176.6 g of methyl 4-hydoxy-3-n-propylbenzoate. A second crop of 166.4 g was obtained by concentrating the filtrate, diluting with hexanes and filtering, bringing the total to 343 g (94.3% yield).

Workup

  1. washthe cake washed with 1 L of methanol
  2. concentrationThe combined filtrate was concentrated
  3. customthe oil flushed with ether
  4. additionHexanes (1.5 L) were added
  5. filtrationThe product was collected by filtration
  6. washwashed with hexanes
  7. customdried

Sources & evidence

ORD record
ord-92a27b40851c478599838cdac6bd5dc3
Source dataset
uspto-grants-1996_09
Patent number
US05559135

Reaction notes

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