4,4'-Dimethoxybenzophenone → Methyl 2,2-Bis-(4-methoxy-phenyl)-6-trifluoromethyl-1,3-benzodioxole-4-carboxylate

HRID 2251610Notes

Reaction equation

HRID 2251610 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.O[C:26]1[C:35]([OH:36])=[CH:34][C:33]([C:37]([F:40])([F:39])[F:38])=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29]>>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][CH:17]=3)[O:36][C:35]3[CH:34]=[C:33]([C:37]([F:38])([F:40])[F:39])[CH:32]=[C:27]([C:28]([O:30][CH3:31])=[O:29])[C:26]=3[O:8]2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 70324,4'-DimethoxybenzophenoneHCID 65578Oxalyl chlorideHCID 59643027Methyl 2,3-dihydroxy-5-trifluoromethyl-benzoate

Product 1

HCID 59642980Methyl 2,2-Bis-(4-methoxy-phenyl)-6-trifluoromethyl-1,3-benzodioxole-4-carboxylate

Procedure

4,4′-Dimethoxybenzophenone (213 mg, 0.88 mmol, 1.5 eq.), oxalyl chloride (900 mg, 7.1 mmol, 8 eq.) and methyl 2,3-dihydroxy-5-trifluoromethyl-benzoate (130 mg, 0.59 mmol, 1 eq.) were reacted according to GP2.2. The crude product was purified using flash chromato-graphy (silica gel, hexane/Et2O 10:1) to yield the title compound as a yellowish, very viscous oil.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-7056ae0e1bad4145b6814b555e7cbf8d
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

Loading…