HCID 15623023, compound → Ethyl 4-(6-acetyl-3-hydroxy-2-propylphenoxy)butanoate

HRID 1493726Notes

Reaction equation

HRID 1493726 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([O:22]CC2C=CC=CC=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([OH:22])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 15623023HCID 15623023, compound

Product 1

HCID 15623024Ethyl 4-(6-acetyl-3-hydroxy-2-propylphenoxy)butanoateYield 70.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 4-(6-acetyl-3-benzyloxy-2-propylphenoxy)butanoate (2.2 g) in ethanol (30 ml) was hydrogenated over 10% palladium on activated carbon (0.45 g) under atmospheric pressure at room temperature. After hydrogen absorption ceased, the catalyst was removed and the solution was evaporated. The residue was purified by silica gel column chromatography, eluting with benzene-ethyl acetate (1:4), to give the title compound (1.2 g, 70.5%) as yellow oil.

Workup

  1. customAfter hydrogen absorption
  2. customthe catalyst was removed
  3. customthe solution was evaporated
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with benzene-ethyl acetate (1:4)

Sources & evidence

ORD record
ord-929a54ef47db44a0821a12e3c6ea3462
Source dataset
uspto-grants-1991_06
Patent number
US05023364

Reaction notes

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