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

HRID 355514Notes

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. Bombay, 7Pt. 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×°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 δ7.62 (s, 1H), 7.30 (d, 1H), 6.85 (d, 1H), 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×°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-10224a7e69bc49bf8b3101caf8a5ce07
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05831073

Reaction notes

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