HCID 18992139, compound → HCID 18992142, compound

HRID 375732Notes

Reaction equation

HRID 375732 reaction equation
[CH2:1]([C:4]1[C:13]([OH:14])=[CH:12][C:11]([OH:15])=[C:10]([CH3:16])[C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:2]=[CH2:3]>[Pd].C(OCC)(=O)C>[OH:15][C:11]1[C:10]([CH3:16])=[C:5]([C:4]([CH2:1][CH2:2][CH3:3])=[C:13]([OH:14])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 1

HCID 18992139HCID 18992139, compound

Product 1

HCID 18992142HCID 18992142, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4.67 g of methyl 2-allyl-3,5-dihydroxy-6-methylbenzoate and 0.23 g of 5% palladium on charcoal in 40 ml of ethyl acetate was hydrogenated for 2 hours at atmospheric pressure. The mixture was filtered and the filtrate evaporated in vacuo. Crystallization of the residue from ethyl acetate/hexane afforded 4.30 g of methyl 3,5-dihydroxy-2-methyl-6-propylbenzoate, m.p. 88°-91° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. customCrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-90a50a8498044cc88df9c19a2137cb2a
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

Loading…