Hydrochloric Acid → 4-(2,4-Dimethyl-3-nitrophenyl)butanoic acid

HRID 1662280Notes

Reaction equation

C([O:3][C:4](=[O:19])[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([N+:15]([O-:17])=[O:16])[C:9]=1[CH3:18])C.Cl>[OH-].[K+]>[CH3:18][C:9]1[C:10]([N+:15]([O-:17])=[O:16])=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=1[CH2:7][CH2:6][CH2:5][C:4]([OH:19])=[O:3]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 4-(2,4-dimethyl-3-nitro-phenyl)-butyric acid ethyl ester (4 g, 16.9 mmol) in 100 ml of 5% KOH was refluxed at 120° C. for 4 hours. This reaction was then cooled to 0° C. and neutralized with 10% HCl to pH 3-4. The resulting solid was filtered and washed with water. After drying under reduced pressure at 40° C., 3.19 g (80%) of pure product as a white solid was obtained. 1H-NMR δ (DMSO-d6, 300 MHz): 12.12 (brs, 1H, exchangeable with D2O), 7.26 (d, J=7.8 Hz, 1H), 7.20 (d, J=7.8 Hz, 1H), 2.61 (t, J=7.8 Hz, 2H), 2.25 (t, J=7.8 Hz, 2H), 2.17 (s, 3H), 2.13 (s, 3H), 1.70 (m, J=7.8 Hz, 2H).

Workup

filtrationThe resulting solid was filtered
washwashed with water
customAfter drying under reduced pressure at 40° C.

Sources & evidence

ORD record: ord-a8dc9521769a4893b7b68a2f31142c61
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030518B2

Reaction notes

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