Water → 2(3H)-Furanone, dihydro-3-(2-nitrobenzoyl)-

HRID 2380079Notes

Reaction equation

HRID 2380079 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9])(=[O:3])[CH3:2].[N+:10]([C:13]1C=[CH:20][CH:19]=[CH:18][C:14]=1C(Cl)=O)([O-:12])=[O:11].O>C1(C)C=CC=CC=1>[N+:10]([C:13]1[CH:14]=[CH:18][CH:19]=[CH:20][C:2]=1[C:1]([CH:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9])=[O:3])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 106012-AcetylbutyrolactoneHCID 118752-Nitrobenzoyl chloride

Product 1

HCID 5917402(3H)-Furanone, dihydro-3-(2-nitrobenzoyl)-Yield 372%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of Mg(OEt)2 (63 g, 0.55 mole) in toluene, under N2, is treated with dihydro-3-acetyl-(3H)-furanone (141 g, 1.10 mole) at 7°-10° C. over a 15 minute period and stirred at 25°-30° C. for 2 hours. The resultant reaction mixture is treated with a solution of o-nitrobenzoyl chloride (185.7 g, 1.0 mole) in toluene at 25°-35° C. over a 45 minute period, stirred at ambient temperatures for 1.75 hours, treated with 400 mL H2O and heated at 60°-75° until reaction is complete by LC analysis. The resultant reaction mixture is cooled to room temperature and the phases are separated to give the title product as a toluene solution, 875 g, 18% desired product by LC analysis (67% yield). The product solution is used as is in Example 6.

Workup

  1. customThe resultant reaction mixture
  2. stirringstirred at ambient temperatures for 1.75 hours
  3. temperatureheated at 60°-75° until reaction
  4. customThe resultant reaction mixture
  5. customthe phases are separated

Sources & evidence

ORD record
ord-105d3767e10b4bd0b9837625a0957bbf
Source dataset
uspto-grants-1994_11
Patent number
US05364968

Reaction notes

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