tert-Butanol → t-butyl N-acryloylcarbamate

HRID 2107549Notes

Reaction equation

HRID 2107549 reaction equation
[C:1]([N:5]=[C:6]=[O:7])(=[O:4])[CH:2]=[CH2:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9]>ClC(Cl)C>[C:1]([NH:5][C:6](=[O:7])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:4])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 15597427Acryloyl isocyanate

Product 1

HCID 14817908t-butyl N-acryloylcarbamate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of acryloyl isocyanate (9.7 g; 100 mmol) in dichloroethane (20 g), a solution of t-butanol (7.4 g; 100 mmol) in dichloroethane (20 g) was dropwise added under ice-cooling in 5 minutes. The solvent was removed by evaporation under reduced pressure to give t-butyl N-acryloylcarbamate as crude crystals, which were recrystallized from chloroform to give colorless needles. M.P., 131°-132° C.

Workup

  1. temperaturecooling in 5 minutes
  2. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7b3ba48bb1d4461387a809bbf2afdb89
Source dataset
uspto-grants-1990_06
Patent number
US04935413

Reaction notes

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