Benzyl Alcohol → benzyl N-ethenylcarbamate

HRID 48364Notes

Reaction equation

HRID 48364 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C=CC(O)=CC=1)[OH:10].[N:17]1[CH:22]=[CH:21]C=C[CH:18]=1>C1(C)C=CC=CC=1>[C:2]1([CH2:1][O:8][C:18]([NH:17][CH:22]=[CH2:21])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 785HydroquinoneHCID 1049Pyridine

Product 1

HCID 10931982benzyl N-ethenylcarbamateYield 878.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Into a 500 mL single neck flask were placed benzyl alcohol (76.5 mL, 792 mmol), hydroquinone (3.05 g, 27.7 mmol), pyridine (3 mL, 27.7 mmol) and the mixture was stirred at 100° C. while treated with the toluene solution of 1-aza-1-diazobuta-1,3-dien-2-one (200 mL) dropwise. The mixture was stirred at 110° C. for 30 minutes and at RT for 12 hours. The reaction mixture was concentrated and the resulting crude oil was distilled under reduced pressure (0.4 mm Hg) to provide the intermediate title compound, (phenylmethoxy)-N-vinylcarboxamide, (43.1 g, 45%) as a pure oil (came out at 110-115° C.) which solidified upon sitting at RT. Electron spray M.S. 178 (M*+H) Analysis for C10H11NO2:

Workup

  1. customInto a 500 mL single neck flask were placed
  2. concentrationThe reaction mixture was concentrated
  3. distillationthe resulting crude oil was distilled under reduced pressure (0.4 mm Hg)

Sources & evidence

ORD record
ord-fdbb5c8477fd45a3b5eb9e57c3a40714
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

Loading…