Acetic Acid → 4-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

HRID 482007

Reaction equation

HRID 482007 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:16])[CH2:12]CC#N)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:17]([OH:20])(=[O:19])[CH3:18]>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=[O:16])[CH2:12][CH2:18][C:17]([OH:20])=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 124916314-(3,4-Dimethoxyphenyl)-4-oxobutanenitrile

Product 1

HCID 2193904-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of 4-(3',4'-dimethoxyphenyl)-4-oxobutyronitrile (111) (2.26 g, 0.01 mol) in acetic acid (15 ml) and hydrochloric acid (12N, 40 ml) was heated at reflux for 1.5 hours and cooled to room temperature. The solvent was removed under reduced pressure to give a brown solid. Recrystallization from water gave 112 as light tan crystals (1.57 g, 66%). 1H NMR (CDCl3) 2.80 (t, J=7.5 Hz, 2H), 3.30 (t, J=7.5 Hz, 2H), 3.94 (s, 3H), 3.96 (s, 3H), 6.89 (d, 1H, J=9 Hz), 7.55 (d, 1H, J=1 Hz) and 7.64 (dd, 1H, 1 and 9 Hz).

Workup

  1. temperatureat reflux for 1.5 hours
  2. customThe solvent was removed under reduced pressure
  3. customto give a brown solid
  4. customRecrystallization from water

Sources & evidence

ORD record
ord-a3430dbd91cd4846a6af4030c3ab5be6
Source dataset
uspto-grants-1998_08
Patent number
US05792776

Linked notes

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