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

HRID 1490247Notes

Reaction equation

HRID 1490247 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-4bd4c39ce46b44b9a09d5270d417f6a0
Source dataset
uspto-grants-1997_10
Patent number
US05681966

Reaction notes

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