Sodium Hydroxide → Ethane-1,1,2-tricarboxylic acid

HRID 978758Notes

Reaction equation

HRID 978758 reaction equation
[CH:1]([C:13]([O:15]CC)=[O:14])([C:8]([O:10]CC)=[O:9])[CH2:2][C:3]([O:5]CC)=[O:4].[OH-].[Na+]>O>[CH:1]([C:13]([OH:15])=[O:14])([C:8]([OH:10])=[O:9])[CH2:2][C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 81961Triethyl ethane-1,1,2-tricarboxylate

Product 1

HCID 313489Ethane-1,1,2-tricarboxylic acidYield 38.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture comprising 49.2 g of triethyl 1,1,2-ethanetricarboxylate, 135 ml of 5N sodium hydroxide and 65 ml of water was stirred at 100° C. for 3 hours, then cooled and concentrated to about 150 ml. A 50 ml portion of cold concentrated hydrochloric acid was added and the mixture was extracted three times with ether. The ether extracts were combined, dried and evaporated, giving 12.5 g of 1,1,2-ethanetricarboxylic acid, mp 169°-170° C.

Workup

  1. temperaturecooled
  2. concentrationconcentrated to about 150 ml
  3. additionA 50 ml portion of cold concentrated hydrochloric acid was added
  4. extractionthe mixture was extracted three times with ether
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-1002bbc4a4b8478c8e7b7a72f149c530
Source dataset
uspto-grants-1987_05
Patent number
US04665210

Reaction notes

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