HCID 18319561, compound → HCID 18319618, compound

HRID 1699385Notes

Reaction equation

HRID 1699385 reaction equation
C([O:8][C:9]1[C:10]([O:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[C:10]([O:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 1

HCID 18319561HCID 18319561, compound

Product 1

HCID 18319618HCID 18319618, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-benzyloxy-2-(3-ethoxycarbonylpropyloxy)benzoate (2.5 g) and palladium on charcoal (0.25 g) in ethanol (12.5 ml) was hydrogenated under hydrogen atmosphere. The catalyst was filtered off. The filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane (1:3) to give colorless oil of ethyl 3-hydroxy-2-(3-ethoxycarbonylpropyloxy)benzoate (1.86 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customThe filtrate was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. additiona mixture of ethyl acetate and n-hexane (1:3)

Sources & evidence

ORD record
ord-1be880ff032241a69ea01630d25ba046
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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