5-[4-(Benzyloxy)-3-methoxyphenyl]penta-2,4-dienoic acid → 5-(4-Hydroxy-3-methoxyphenyl)pentanoic acid

HRID 1195947Notes

Reaction equation

HRID 1195947 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[CH:11][C:10]=1[O:22][CH3:23])C1C=CC=CC=1.[H][H]>CN(C)C=O.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:11][C:10]=1[O:22][CH3:23]

Participants

5

Reactant 2

HCID 542250435-[4-(Benzyloxy)-3-methoxyphenyl]penta-2,4-dienoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 2404525-(4-Hydroxy-3-methoxyphenyl)pentanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The raw product obtained in Example 21 was dissolved in 500 ml of N,N-dimethylformamide and 22 g of 10% palladium on charcoal catalyst was added. The mixture was hydrogenated at 60° C. and normal pressure until the theoretical amount (3 mole) of hydrogen was consumed. After filtering the solvent was evaporated in vacuo to a great extent and the residue was dissolved in 1 l of dichloromethane and washed with 2 l of water. The product was extracted with 1.5 l of saturated NaHCO3 -solution. After acidification of the aqueous phase with hydrochloric acid the product was extracted with 1 l of dichloromethane. The solvent was distilled off in vacuo and the semisolid residue (180 g) was used to the next step.

Workup

  1. customwas hydrogenated at 60° C.
  2. filtrationAfter filtering the solvent
  3. customwas evaporated in vacuo to a great extent
  4. dissolutionthe residue was dissolved in 1 l of dichloromethane
  5. washwashed with 2 l of water
  6. extractionThe product was extracted with 1.5 l of saturated NaHCO3 -solution
  7. extractionAfter acidification of the aqueous phase with hydrochloric acid the product was extracted with 1 l of dichloromethane
  8. distillationThe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-e0b4c5e1e52c4f7aadfcb893a89baaa3
Source dataset
uspto-grants-1992_05
Patent number
US05112861

Reaction notes

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