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

HRID 1847590Notes

Reaction equation

HRID 1847590 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, 0.31 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-f2175c74ee724a0fa68438555bbb309e
Source dataset
uspto-grants-2015_02
Patent number
US08952050B2

Reaction notes

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