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

HRID 865539Notes

Reaction equation

HRID 865539 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-hydoxybenzoate in 1.5 L of methanol was hydrogenated for 1 hr in a ParrR 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 Sulka-FlocR 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-985fd89fefb1488892f4143873ef2d59
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Reaction notes

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