Benzyl Alcohol → benzyl N-methacryloylcarbamate

HRID 2107537Notes

Reaction equation

HRID 2107537 reaction equation
[C:1]([N:6]=[C:7]=[O:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCCl>[C:1]([NH:6][C:7](=[O:8])[O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 10942374Methacryloyl isocyanate

Product 1

HCID 11321946benzyl N-methacryloylcarbamate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of methacryloyl isocyanate (11.1 g; 0.1 mol) in 1,2-dichloroethane (50 ml) was dropise added to dry benzyl alcohol (10.8 g; 0.1 mol) under nitrogen stream while cooling with ice. After completion of the addition, 1,2-dichloroethane was evaporated under reduced pressure. The residue (21.8 g) was recrystallized from a mixture of hexane and benzene to give benzyl N-methacryloylcarbamate as colorless needles. M.P., 109°-110° C.

Workup

  1. temperaturewhile cooling with ice
  2. customwas evaporated under reduced pressure
  3. customThe residue (21.8 g) was recrystallized from a mixture of hexane and benzene

Sources & evidence

ORD record
ord-1934666ca4ca44c1bbd837f5b1c0b49c
Source dataset
uspto-grants-1990_06
Patent number
US04935413

Reaction notes

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