Sulfuric Acid → Benzenepropanoic acid, beta-oxo-3-(trifluoromethoxy)-

HRID 1745554Notes

Reaction equation

HRID 1745554 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8].C(O[Si](C)(C)C)(=O)[CH2:16][C:17]([O:19][Si](C)(C)C)=[O:18].[Li+].[Br-].OS(O)(=O)=O.[C:37]([O:40][C:41]([CH3:43])=[CH2:42])(=[O:39])[CH3:38]>CC#N.CCN(CC)CC>[O:8]=[C:7]([C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([O:3][C:2]([F:14])([F:13])[F:1])[CH:5]=1)[CH2:16][C:17]([OH:19])=[O:18].[CH3:42][C:41]1([CH3:43])[O:40][C:37](=[O:39])[CH:38]=[C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([O:3][C:2]([F:14])([F:13])[F:1])[CH:5]=2)[O:8]1

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 7916Isopropenyl acetateHCID 82050Lithium BromideHCID 87656Bis(trimethylsilyl) malonateHCID 5228543-(Trifluoromethoxy)benzoyl chloride

Product 2

HCID 22224559Benzenepropanoic acid, beta-oxo-3-(trifluoromethoxy)-HCID 222247282,2-Dimethyl-6-(3-trifluoromethoxy-phenyl)-[1,3]dioxin-4-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

The 3-oxo-3-(3-trifluoromethoxy-phenyl)-propionic acid was prepared from 3-trifluoromethoxybenzoyl chloride and bis(trimethylsilyl) malonate with Et3N and LiBr in CH3CN at 0° C. according to general procedure H (method c1). The crude material was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as an orange solid (2.27 g).

Sources & evidence

ORD record
ord-5e981e074a0440eab3a82ad00f743c2a
Source dataset
uspto-grants-2006_03
Patent number
US07018998B2

Reaction notes

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