Water → 4-(3-Methylphenyl)-4-oxobutyric acid

HRID 2396566Notes

Reaction equation

[CH:1]1[C:6](O)=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:9]1(=[O:15])[O:14][C:12](=[O:13])[CH2:11][CH2:10]1.[Cl-].[Al+3].[Cl-].[Cl-].O>ClC(Cl)C(Cl)Cl.CCOCC>[CH3:8][C:3]1[CH:2]=[CH:1][CH:6]=[C:5]([CH:4]=1)[C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:15]

Participants

Conditions

Temperature: 60 °C

Procedure

This compound was prepared by the method of Raval et al., J. Univ. Bombary, 7, Pt. 3, 184 (1983); CA 33, 3779 (1989). p-Cresol (4.0 g, 37 mmol) and succinic anhydride (3.4 g, 34 mmol) were combined in 1,1,2,2-tetrachloroethane (40 mL) and the mixture was heated to 60° C. Aluminum chloride (9.5 g, 71 mmol) was then added to the solution at a rate of 2 g/20 min. Once this was complete the reaction was heated to 135° C. for 30 min. After cooling, water and ether (30 mL of each) were added and the aqueous layer was extracted with 3×20 mL of ether. The combined organic fractions were dried and the remaining residue was purified by flash silica chromatography to yield 2.2 g (28.5%). 1H NMR δ 7.62 (s, 1H), 7.30 (d, 1H), 6.85 (d, 1 H), 3.32 (t, 2H), 2.35 (t, 2H), 2.22 (s, 1H).

Workup

customThis compound was prepared by the method of Raval et al., J
temperatureOnce this was complete the reaction was heated to 135° C. for 30 min
temperatureAfter cooling
extractionthe aqueous layer was extracted with 3×20 mL of ether
customThe combined organic fractions were dried
customthe remaining residue was purified by flash silica chromatography
customto yield 2.2 g (28.5%)

Sources & evidence

ORD record: ord-1f34b7f70ed4451d918057029fb0b57d
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05493012

Reaction notes

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