4-Methoxyphenylacetic Acid → 2-(4-(Benzyloxy)phenyl)-2-oxoethyl 2-(4-methoxyphenyl)acetate

HRID 446809Notes

Reaction equation

HRID 446809 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:36])[CH2:28]CC2C=CC=CC=2)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:28][C:27]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:22][CH:23]=2)=[O:36])=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 76904-Methoxyphenylacetic AcidHCID 149668391-(4-(Benzyloxy)phenyl)-3-phenylpropan-1-one

Product 1

HCID 583680092-(4-(Benzyloxy)phenyl)-2-oxoethyl 2-(4-methoxyphenyl)acetateYield 128.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-(4-methoxyphenyl)acetic acid (3 g, 0.01 mol) in acetonitrile (60 mL) were added TEA (16.5 mL, 0.129 mol) and 1-(4-(benzyloxy)phenyl)-3-phenylpropan-1-one (6.6 g, 0.02 mol). The reaction mixture was stirred at RT for 16 h, concentrated in vacuo and the resulting residue was extracted with EtOAc (2×100 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to afford 2-(4-(benzyloxy)phenyl)-2-oxoethyl 2-(4-methoxyphenyl)acetate (5 g, 71%) as a brown solid.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionthe resulting residue was extracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c13c451414ec42d492510806638fdae8
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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