Methanesulfonic Acid → tert-Butyl 2-chloroacrylate

HRID 1368799Notes

Reaction equation

HRID 1368799 reaction equation
[Cl:1][C:2](=[CH2:6])[C:3]([OH:5])=[O:4].CS(O)(=O)=O.[CH3:12][C:13](=[CH2:15])[CH3:14].C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2](=[CH2:6])[C:3]([O:5][C:13]([CH3:15])([CH3:14])[CH3:12])=[O:4]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8255IsobutyleneHCID 117352-Chloroacrylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 3085699tert-Butyl 2-chloroacrylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

32 g of α-chloroacrylic acid was dissolved in 600 ml of dichloromethane and, to this, 20 ml of methanesulphonic acid and 300 ml of isobutylene were added at −5° C. After stirring for 30 hours at room temperature, the reaction liquid was poured into 500 ml of saturated aqueous sodium bicarbonate solution and the dichloromethane layer separated off. After drying with anhydrous sodium sulphate, the solvent was distilled off and t-butyl α-chloroacrylate obtained. 10 g of the t-butyl α-chloroacrylate obtained plus 200 mg of azobisisobutyronitrile were dissolved in 100 ml of toluene and reaction carried out at 80° C. Poly-t-butyl α-chloroacrylate was obtained. The molecular weight of the copolymer obtained determined by gel permeation chromatography (GPC) was, by polystyrene conversion, a number average molecular weight of 215,000 and a weight average molecular weight of 537,000. The polymer obtained was irradiated with an electron beam, and the value of the main chain scission efficiency Gs calculated from the number average molecular weight determined by GPC was 3.8.

Workup

  1. customthe reaction liquid
  2. customthe dichloromethane layer separated off
  3. dry with materialAfter drying with anhydrous sodium sulphate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-86ad1acd23f24b84a24a0fcf78d7ea23
Source dataset
uspto-grants-2003_06
Patent number
US06576400B1

Reaction notes

Loading…