Sulfuric Acid → 1,1-Cyclopropanedicarboxylic acid

HRID 1820613Notes

Reaction equation

HRID 1820613 reaction equation
C([C:3]([CH2:10][CH3:11])([C:7]([O-:9])=[O:8])[C:4]([O-:6])=[O:5])C.BrCCBr.S(=O)(=O)(O)O>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:3]1([C:7]([OH:9])=[O:8])([C:4]([OH:6])=[O:5])[CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 78391,2-DibromoethaneHCID 69515632,2-Diethylpropanedioate

Product 1

HCID 690171,1-Cyclopropanedicarboxylic acidYield 50.2%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

In 50% NaOH 187 ml was dissolved 15 g of diethylmalonate at room temperature. Benzyltriethylammoniumchloride (21.3 g) was added and the resulting mixture was stirred for 10 minutes. 1,2-Dibromoethane (12.3 g) was added to the reaction solution and the resulting mixture was stirred for more than 18 hours at room temperature. The reaction mixture was neutralized by adding dropwise conc. sulfuric acid and then extracted with ethyl acetate. The extract was distilled under reduced pressure to give 6.2 g of the title compound as a white solid.

Workup

  1. stirringthe resulting mixture was stirred for more than 18 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. distillationThe extract was distilled under reduced pressure

Sources & evidence

ORD record
ord-b3250061be35405098f4d41c2bf44931
Source dataset
uspto-grants-2009_10
Patent number
US07605147B2

Reaction notes

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