Methyl Isocyanate → HCID 20396653, compound

HRID 972114Notes

Reaction equation

HRID 972114 reaction equation
[CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH3:13])[CH:9]=[C:10]([OH:12])[CH:11]=1.[CH3:16][N:17]=[C:18]=[O:19]>C(N(CC)CC)C.C1C=CC=CC=1>[CH3:16][NH:17][C:18](=[O:19])[O:12][C:10]1[CH:9]=[C:8]([CH3:13])[CH:7]=[C:6]([O:5][CH2:4][CH:3]([O:2][CH3:1])[O:14][CH3:15])[CH:11]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 20396681HCID 20396681, compound

Product 1

HCID 20396653HCID 20396653, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent2×

Procedure

3-(2,2-Dimethoxyethoxy)-5-hydroxytoluene (2.50 grams), benzene (50 ml) and triethylamine (4 drops) were charged into a glass reaction vessel equipped with a mechanical stirrer. Methyl isocyanate (1.0 ml) was added to the vessel, and the resulting mixture was stirred at room temperature for a period of about 2 hours. The mixture was then allowed to stand at ambient temperature over the weekend. After this time the reaction mixture was stripped of benzene, leaving a viscous liquid residue. This residue was distilled under vacuum to yield the desired product O-[3-(2,2-dimethoxyethoxy)-5-methylphenyl] N-methylcarbamate as an oil.

Workup

  1. customequipped with a mechanical stirrer
  2. customto stand at ambient temperature over the weekend
  3. customleaving a viscous liquid residue
  4. distillationThis residue was distilled under vacuum

Sources & evidence

ORD record
ord-6f0db323dcd84a25850e244e9aa31808
Source dataset
uspto-grants-1979_07
Patent number
US04163112

Reaction notes

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