Cyclobutanone → Chromanone

HRID 2103022Notes

Reaction equation

HRID 2103022 reaction equation
C(O[C:5]1[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[C:8]([OH:14])=[C:7](C)[C:6]=1C)(=O)C.[C:17]1(=O)CCC1.N1CCCC1>C1(C)C=CC=CC=1>[CH:5]1[CH:6]=[CH:7][C:8]2[O:14][CH2:17][CH2:12][C:11](=[O:13])[C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 31268PyrrolidineHCID 9794488HCID 9794488, compound

Product 1

HCID 68110Chromanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3-Dimethyl-1,4-phenylene diacetate (5.5 g) was heated up with boron trifluoride-acetic acid complex (25 mL) at 120° C. for 5 hours. The mixture was poured into ice, and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate water solution to pH about 7. Evaporation gave 5.5 g of 5-acetyl-4-hydroxy-2,3-dimethylphenyl acetate as yellow solid. Refluxing 5-acetyl-4-hydroxy-2,3-dimethylphenyl acetate (5.5 g) with cyclobutanone (1.9 g, 27 mmol) and pyrrolidine (2.1 mL, 24.8 mmol) in toluene failed to give chromanone but gave 3.4 g of 1-(2,5-dihydroxy-3,4-dimethylphenyl)-ethanone as a solid.

Sources & evidence

ORD record
ord-8865cc9f0309425a8065976c380b62a8
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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