Methanol → Propanoic acid, 3-chloro-2,2-dimethyl-, methyl ester

HRID 1632118Notes

Reaction equation

HRID 1632118 reaction equation
[Cl:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](Cl)=[O:5].C(N(CC)CC)C.[CH3:16][OH:17]>>[Cl:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([O:17][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 613453-Chloro-2,2-dimethylpropanoyl chloride

Product 1

HCID 543185Propanoic acid, 3-chloro-2,2-dimethyl-, methyl ester

Procedure

219 g of chloropivaloyl chloride was added drop-by-drop to a chilled (0°-5° C.), stirred solution of 141.4 g of triethylamine in 320 g of anhydrous methanol. The resulting mixture was warmed to room temperature in one hour, and most of the methanol was evaporated under reduced pressure. The residue was mixed with water and extracted with ether. The extract was dried (MgSO4), and the solvent was evaporated. The residue was distilled to give methyl 3-chloro-2,2-dimethylpropionate (3A), b.p.: 40°-50° C. (14 Torr.).

Workup

  1. temperaturea chilled (0°-5° C.)
  2. custommost of the methanol was evaporated under reduced pressure
  3. additionThe residue was mixed with water
  4. extractionextracted with ether
  5. dry with materialThe extract was dried (MgSO4)
  6. customthe solvent was evaporated
  7. distillationThe residue was distilled

Sources & evidence

ORD record
ord-c7a50dcc66724a2796590abdda9c6f3b
Source dataset
uspto-grants-1984_10
Patent number
US04474598

Reaction notes

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