Potassium Hydroxide → 4-(4-Chlorophenyl)butyric acid

HRID 2188421Notes

Reaction equation

[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=O)=[CH:4][CH:3]=1.[OH-].[K+].O.NN>C(O)COCCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 3-(4-chlorobenzoyl) propionic acid (34) (2.50 g, 12.0 mmol), KOH (s) (1.75 g, 31.2 mmol), and hydrazine monohydrate (1.25 mL, 25.8 mmol) in 12.5 mL of diethylene glycol was refluxed azeotropically at 120-130° C. for 90 min to remove water. The reaction mixture was then refluxed at 170° C. for 3 h, cooled to RT, diluted with 12.5 mL of water, and poured into 15 mL 2.5 N HCl(aq). The precipate was filtered off, dissolved in CH2Cl2, and the solvent removed to give 35a (2.23 g, 96%) as a white solid. UV λmax 223 (8980, 95% ETHANOL); 1H NMR (400 MHz, CDCl3) δ 7.26 (d, J=7 Hz, 2H), 7.12 (d, J=8 Hz, 2H), 2.66 (t, J=4 Hz, 2H), 2.38 (t, J=4 Hz, 2H), 1.96 (m, 2H); 13C NMR (CDCl3) δ 179.3, 140.0, 132.2, 130.2, 128.9, 34.7, 33.4, 26.4; IR (drift) 3063 (s), 3051 (s), 2955 (s), 2923 (s,b), 2905 (s), 2814, 2797, 2493 (b), 2466, 2413, 2367 (b), 2321, 1706 (s), 1492 (s), 1212 (s), cm−1; MS (EI) m/z (rel. intensity) 198 (M+, 22), 200 (7), 198 (22), 140 (32), 139 (17), 138 (99), 127 (15), 125 (48), 103 (10), 89 (13), 60 (9); HRMS (EI) calcd for 198.0448, found 198.0441.

Workup

customto remove water
temperatureThe reaction mixture was then refluxed at 170° C. for 3 h
temperaturecooled to RT
additiondiluted with 12.5 mL of water
additionpoured into 15 mL 2.5 N HCl(aq)
filtrationThe precipate was filtered off
dissolutiondissolved in CH2Cl2
customthe solvent removed

Sources & evidence

ORD record: ord-35decb90188f41a6bd5b3c7fc13d93a6
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410585B1

Reaction notes

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