3-Chloro-2,2-dimethylpropanoyl chloride → Tert-butyl 3-chloropivaloate

HRID 1586767Notes

Reaction equation

HRID 1586767 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[Na+].[Cl:7][CH2:8][C:9]([CH3:14])([CH3:13])[C:10](Cl)=[O:11]>C1(C)C=CC=CC=1>[Cl:7][CH2:8][C:9]([CH3:14])([CH3:13])[C:10]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[O:11]

Participants

4

Reactant 2

HCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 23676156Sodium t-butoxide

Product 1

HCID 22590969Tert-butyl 3-chloropivaloate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A slurry of sodium tert-butoxide (195.3 g, 2.03 mol) in 800 mL of dry toluene was cooled to 0° C. in an ice bath. To the stirred slurry was added 3-chloropivaloyl chloride (XIII) (300.0 g 1.94 mol) dropwise at a rate sufficient to maintain the reaction temperature below 10° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water, the mixture extracted with ether, and the ether layer washed with water and saturated NaHCO3. After drying over MgSO4, the solution was filtered and concentrated to give the product as an amber oil. 1H NMR (CDCl3) δ 1.24 (s,6H), 1.46 (s,9H), 3.57 (s,2H); 13C NMR (CDCl3) δ 22.96, 27.70, 44.80, 53.32, 80.87, 174.5.

Workup

  1. temperatureto maintain the reaction temperature below 10° C
  2. additionAfter the addition
  3. customThe reaction was quenched with water
  4. extractionthe mixture extracted with ether
  5. washthe ether layer washed with water and saturated NaHCO3
  6. dry with materialAfter drying over MgSO4
  7. filtrationthe solution was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e03e573447c74a7dbbb31a0e40d8e10c
Source dataset
uspto-grants-1993_06
Patent number
US05216022

Reaction notes

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