Water → 1-(2-Methylphenyl)pentane-1,4-dione

HRID 917658Notes

Reaction equation

[C:1]1([CH3:9])[C:2]([CH:7]=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH:10]([C:12]([CH3:14])=[O:13])=[CH2:11].C(N(CC)CC)C.O>[Br-].C([N+]1C(C)=C(CCO)SC=1)C.CN(C=O)C>[CH3:9][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[O:8])[CH2:11][CH2:10][C:12](=[O:13])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

25 g (208 mmol) of o-tolualdehyde, 14.58 g (208 mmol) of methyl vinyl ketone, 21.05 g (208 mmol) of triethylamine, 5.4 g (21.4 mmol) of 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide were dissolved in this order in 100 ml of DMF and stirred at 80° C. for 12 hours. The reaction mixture was subsequently admixed with 400 ml of water and extracted twice with methylene chloride. The combined methylene chloride phases were washed with 10% strength sulfuric acid and saturated sodium hydrogencarbonate solution and dried over sodium sulfate. After taking off the solvent on a rotary evaporator, the product was purified by fractional distillation.

Workup

extractionextracted twice with methylene chloride
washThe combined methylene chloride phases were washed with 10% strength sulfuric acid and saturated sodium hydrogencarbonate solution
dry with materialdried over sodium sulfate
customon a rotary evaporator
distillationthe product was purified by fractional distillation

Sources & evidence

ORD record: ord-b92715fdf1c4412081af3c16dd8b53bf
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273940B2

Reaction notes

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