2-Chloro-1,3,5-trimethylbenzene → HCID 5781145, compound

HRID 2360111Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:21])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[O:19][CH3:20].[C:22]1(C)C=C(C)C=C(C)C=1Cl>CN(C=O)C>[CH3:20][O:19][C:12]1[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=1[C:10]1[C:9](=[O:21])[C:3]2[C:2](=[CH:7][C:6]([OH:8])=[CH:5][CH:4]=2)[O:1][CH:22]=1

Participants

Conditions

Temperature: 110 °C

Procedure

BF3—OEt2 complex (14 ml, 112 mmol) was gradually added to a solution of 1-(2,4-dihydroxy-phenyl)-2-(2,4-dimethoxy-phenyl)-ethanone (8.1 gm, 28 mmol) in DMF at 0° C. The resulting solution was stirred for 30 min. Mesityl chloride (6.5 ml, 84 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 3-(2,4-dimethoxy-phenyl)-7-hydroxy-chromen-4-one (5.9 gm, 70%) 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-dadaef6c58594178ace75397f8fa3476
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686028B2

Reaction notes

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