2-Chloro-1,3,5-trimethylbenzene → HCID 58030372, compound

HRID 2360104Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

BF3—OEt2 complex (7 ml, 56 mmol) was gradually added to a solution of 2-(2-methoxy-phenyl)-1-(2,3,4-trihydroxy-phenyl)-ethanone (3.8 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 7,8-dihydroxy-3-(2-methoxy-phenyl)-chromen-4-one (0.98 gm, 25%) 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-a9deb842dd8449c597bc2e07b387c169
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686028B2

Reaction notes

Loading…