Acetic Anhydride → Butyl 2-methylene-3-acetoxy-4,4,4-trichlorobutyrate

HRID 382850Notes

Reaction equation

HRID 382850 reaction equation
[CH2:1]=[C:2]([CH:10]([OH:15])[C:11]([Cl:14])([Cl:13])[Cl:12])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4].[C:16](OC(=O)C)(=[O:18])[CH3:17].C([O-])(=O)C.[Na+]>C([O-])(=O)C.[Na+].C(O)(=O)C>[CH2:1]=[C:2]([CH:10]([O:15][C:16](=[O:18])[CH3:17])[C:11]([Cl:14])([Cl:13])[Cl:12])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4]

Participants

6

Reactant 3

HCID 7918Acetic Anhydride2×HCID 517045Sodium AcetateHCID 18362110HCID 18362110, compound

Product 1

HCID 11220844Butyl 2-methylene-3-acetoxy-4,4,4-trichlorobutyrateYield 91.4%

Reagents, catalysts & solvents 2

HCID 517045Sodium AcetateCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To 1173.0 g of butyl 2-methylene-3-hydroxy-4,4,4-trichlorobutyrate (91% pure) charged in a 2-liter, 3-neck round bottom flask equipped with a mechanical stirrer, thermometer, and a condenser were added 520.0 g of acetic anhydride and 7.0 g of sodium acetate. The reaction mixture was heated at 120° C. for three hours. Unreacted acetic anhydride and formed acetic acid were stripped off under vacuum at <80° C./0.6 mm Hg. After cooling to room temperature, the solid sodium acetate that had settled to the bottom of the flask was separated. 1236.1 g of acetylated product was obtained, 91.3% purity (GC analysis), 91.4% yield. The product structure was confirmed by NMR spectroscopy.

Workup

  1. customequipped with a mechanical stirrer
  2. customwere stripped off under vacuum at <80° C.
  3. temperatureAfter cooling to room temperature
  4. customwas separated

Sources & evidence

ORD record
ord-457871aa308a437d8d54dc4a146eb30b
Source dataset
uspto-grants-2001_10
Patent number
US06310237B1

Reaction notes

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