tert-Butyl methyl ether → Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

HRID 1893166Notes

Reaction equation

HRID 1893166 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[C:16](\[O:20][CH2:21][CH3:22])/[C:17]([O-:19])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.CO[C:25](C)(C)[CH3:26]>[Pd]>[CH2:25]([O:19][C:17](=[O:18])[CH:16]([O:20][CH2:21][CH3:22])[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1)[CH3:26]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 86645619HCID 86645619, compound

Product 1

HCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoateYield 99%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Ethyl E/Z-3-(4-benzyloxyphenyl)-2-ethoxyacrylate (20.0 g, 61.3 mmol) dissolved in tert-butyl methyl ether (40 mL) charged with palladium on carbon (5%) (1.0 g, Engelhard Tech code no. 4531) was hydrogenated with vigorous stirring at atmospheric pressure at room temperature for 2-3 days. The catalyst was filtered off and washed with a few milliliters of tent-butyl methyl ether. The combined filtrates were concentrated in vacuo to yield 14.5 g (99% yield) of the title compound as a viscous oil, which crystallizes upon standin.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with a few milliliters of tent-butyl methyl ether
  3. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-e57929bd41c241bb967bcdff70a34dfd
Source dataset
uspto-grants-2013_08
Patent number
US08513233B2

Reaction notes

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