Methanol → 1,1-Cyclopropanedicarboxylic acid

HRID 1458314Notes

Reaction equation

HRID 1458314 reaction equation
CO.[OH-].[K+].[C:5]1([C:12]([O:14]C)=[O:13])([C:8]([O:10]C)=[O:9])[CH2:7][CH2:6]1.S(=O)(=O)(O)O>O>[C:5]1([C:12]([OH:14])=[O:13])([C:8]([OH:10])=[O:9])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 27695391,1-Cyclopropanedicarboxylic acid, 1,1-dimethyl ester

Product 1

HCID 690171,1-Cyclopropanedicarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 4 liter multinecked flask, 800 ml of aqueous saturated K2 SO4 solution (from previous batches, neutralized), 500 ml of methanol and 330 g of KOH (85%, 5.0 mol) are heated and then, at 68° C., over a period of 90 minutes, a 316.2 g amount of dimethyl cyclopropane-1,1-dicarboxylate (2.0 mol) is added gradually. During the postreaction time of 4 hours, some of the methanol distills. After the reaction solution has cooled it is acidified, with cooling, with a 281 g amount of sulfuric acid (96% strength, 2.75 mol) which has previously been diluted with 100 ml of water. The K2SO4 which crystallizes is filtered via a sintered disk, washed with methanol and dried: 380 g (87.2% of the theoretical yield).

Workup

  1. distillationDuring the postreaction time of 4 hours, some of the methanol distills
  2. temperatureAfter the reaction solution has cooled it
  3. customThe K2SO4 which crystallizes
  4. filtrationis filtered via a sintered disk
  5. washwashed with methanol
  6. customdried
  7. custom380 g (87.2% of the theoretical yield)

Sources & evidence

ORD record
ord-5dac835174e84bae98c287f2520d5769
Source dataset
uspto-grants-1998_12
Patent number
US05849949

Reaction notes

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