2-Chloro-1,3,5-trimethylbenzene → HCID 58913587, compound

HRID 2360106Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:20])=[CH:4][C:5]([OH:19])=[C:6]([C:8](=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH:7]=1.[C:21]1(C)C=C(C)C=C(C)C=1Cl>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[OH:20])[O:19][CH:21]=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])[C:8]2=[O:18]

Participants

Conditions

Temperature: 110 °C

Procedure

BF3—OEt2 complex (7 ml, 56 mmol) was gradually added to a solution of 1-(5-chloro-2,4-dihydroxy-phenyl)-2-(2-methoxy-phenyl)-ethanone (4.1 gm, 14 mmol) in DMF at 0° C. The resulting solution was stirred for 30 min. Mesityl chloride (1.5 ml, 42 mmol) was then gradually added to it at 50° C. The solution was then heated up to 110° C. for 5 hours. The mixture was then concentrated. The residue was treated with ice and the solid obtained was purified with silica gel column chromatography using hexane-chloroform as the eluent to give 6-chloro-7-hydroxy-3-(2-methoxy-phenyl)-chromen-4-one (2.5 gm, 60%) as white solid.

Workup

concentrationThe mixture was then concentrated
additionThe residue was treated with ice
customthe solid obtained
customwas purified with silica gel column chromatography

Sources & evidence

ORD record: ord-72c9d66782d34fa3b33e4ae324a576d0
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686028B2

Reaction notes

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