Ethanol → Ethyl 3-(4-phenoxyphenyl)propanoate

HRID 386432Notes

Reaction equation

HRID 386432 reaction equation
C([C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=1)C1C=CC=CC=1.[CH3:21][CH2:22][OH:23]>[Pd]>[O:23]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:13]=1)[C:22]1[CH:10]=[CH:9][CH:8]=[CH:13][CH:21]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 67528407ethyl (E)-3-(4-benzylphenyl)acrylate

Product 1

HCID 20213313Ethyl 3-(4-phenoxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
25 °C

Procedure

A solution of ethyl (E)-3-(4-benzylphenyl)acrylate (S28, 500 mg, 1.97 mmol) in EtOH (20 mL) was treated with 10% Pd/C (45 mg) and purged with H2. The reaction mixture was stirred overnight at 25° C., filtered through Celite and concentrated to afford S29 (502 mg, 1.96 mmol, 99%) as a yellow oil: 1H NMR (CDCl3, 500 MHz) 7.34 (dd, 2H, J=8.4, 7.4 Hz), 7.17 (d, 2H, J=8.4 Hz), 7.09 (dt, 1H, J=7.7, 1.1 Hz), 7.00 (dd, 2H, J=8.8, 1.1 Hz), 6.95 (d, 2H, J=8.8 Hz), 4.14 (q, 2H, J=7.0 Hz), 2.94 (t, 2H, J=7.7 Hz), 2.63 (t, 2H, J=7.7 Hz), 1.25 (t, 3H, J=7.0 Hz).

Workup

  1. custompurged with H2
  2. filtrationfiltered through Celite
  3. concentrationconcentrated
  4. customto afford S29 (502 mg, 1.96 mmol, 99%) as a yellow oil

Sources & evidence

ORD record
ord-c214653dd1694eeb9e555beb8f0127f8
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

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