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

HRID 1956611Notes

Reaction equation

HRID 1956611 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-6e2a846b04384d0099bfd4324152c593
Source dataset
uspto-grants-1998_07
Patent number
US05780503

Reaction notes

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