Sulfuric Acid → 6-(3-Chloro-phenyl)-2,2-dimethyl-[1,3]dioxin-4-one

HRID 1062021Notes

Reaction equation

HRID 1062021 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].C[Si]([C:15]([Si](C)(C)C)([C:19]([O-:21])=[O:20])[C:16]([O-:18])=[O:17])(C)C.CCN([CH2:31][CH3:32])CC.[Li+].[Br-].OS(O)(=O)=O.[CH3:40]C#N>C(OC(C)=C)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH2:15][C:16]([OH:18])=[O:17])[CH:8]=[CH:9][CH:10]=1.[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][C:31]([CH3:32])([CH3:40])[O:21][C:19](=[O:20])[CH:15]=2)[CH:8]=[CH:9][CH:10]=1

Participants

9

Reactant 6

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 82050Lithium BromideHCID 222245802,2-Bis(trimethylsilyl)propanedioate

Product 2

HCID 222246906-(3-Chloro-phenyl)-2,2-dimethyl-[1,3]dioxin-4-oneHCID 222247783-Chlorobenzoylacetic acid

Reagents, catalysts & solvents 1

HCID 7916Isopropenyl acetateSolvent

Procedure

The 3-(3-chloro-phenyl)-3-oxo-propionic acid was prepared from 3-chlorobenzoyl chloride (11 mL, 85.7 mmol) and bis(trimethylsilyl)malonate (23.0 mL, 90.0 mmol) with Et3N (25 mL, 180 mmol) and LiBr (8.19 g, 94.3 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (17.1 g) was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as a yellow-brown solid (8.0 g).

Sources & evidence

ORD record
ord-7248faeb596f44fb852cceeb3be6075e
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Reaction notes

Loading…