Sodium Hydroxide → 3-Chloro-2,2-dimethylbut-3-enoic acid

HRID 468517Notes

Reaction equation

HRID 468517 reaction equation
[Cl:1][C:2](=[CH2:10])[C:3]([CH3:9])([CH3:8])[C:4]([O:6]C)=[O:5].[OH-].[Na+]>O>[Cl:1][C:2](=[CH2:10])[C:3]([CH3:9])([CH3:8])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 40423475Methyl 3-chloro-2,2-dimethylbut-3-enoate

Product 1

HCID 404234773-Chloro-2,2-dimethylbut-3-enoic acidYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-chloro-2,2-dimethylbut-3-enoate (42.0 g, 0.26 mol) and NaOH (12.4 g, 031 mol) in water (300 mL) was heated at reflux overnight. After cooling, the reaction mixture was extracted with ether. The organic layer contained 20 g of methyl 3-chloro-2,2-dimethylbut-3-enoate (48% recovered). The aqueous layer was acidified with cold 20% HCl solution and was extracted with ether (250 mL×3). The combined organic layers were dried and evaporated under reduced pressure to give 3-chloro-2,2-dimethylbut-3-enoic acid (17 g, 44%), which was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with ether
  5. extractionwas extracted with ether (250 mL×3)
  6. customThe combined organic layers were dried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c673632a67c3427986008d179b470cd2
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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