Sulfuric Acid → 2-Carboxy-2,4-dimethylcyclopent-4-en-5-olone

HRID 2058623Notes

Reaction equation

HRID 2058623 reaction equation
[C:1]([C:6]1([CH3:14])[CH2:10][C:9]([CH3:11])=[C:8]([OH:12])[C:7]1=[O:13])([O:3]CC)=[O:2].[OH-].[Na+].S(=O)(=O)(O)O>>[C:1]([C:6]1([CH3:14])[CH2:10][C:9]([CH3:11])=[C:8]([OH:12])[C:7]1=[O:13])([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 204720932-Carboethoxy-2,4-dimethylcyclopent-4-en-5-olone

Product 1

HCID 204720912-Carboxy-2,4-dimethylcyclopent-4-en-5-oloneYield 73.5%

Procedure

4.8 g (24 mmol) of the foregoing 2-carboethoxy-2,4-dimethylcyclopent-4-en-5-olone are treated with 48 ml of 2N sodium hydroxide solution and the mixture is stirred at room temperature for 1.5 hours. For the working-up, the mixture is adjusted to pH 3 with 10% sulphuric acid and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate, concentrated and dried in a high vacuum for 2 hours. There are obtained 3 g (58.5%) of 2-carboxy-2,4-dimethylcyclopent-4-en-5-olone of melting point 98°-105° C., with elimination of carbon dioxide.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated
  4. customdried in a high vacuum for 2 hours

Sources & evidence

ORD record
ord-e386304a65b24cb2ba931580658b432b
Source dataset
uspto-grants-1982_03
Patent number
US04318855

Reaction notes

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