Guaiacol → 2-Methoxyphenyl chloroformate

HRID 6903

Reaction equation

HRID 6903 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1O.CN(C)C1C=CC=CC=1.[C:19]([Cl:22])(Cl)=[O:20].CN(C=[O:27])C>C1(C)C=CC=CC=1.ClC1C=CC=CC=1>[Cl:22][C:19]([O:20][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:27]

Participants

7

Reactant 4

HCID 460GuaiacolHCID 949N,N-DimethylanilineHCID 6228DimethylformamideHCID 6371Phosgene

Product 1

HCID 33621432-Methoxyphenyl chloroformateYield 50%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7964ChlorobenzeneSolvent

Procedure

A solution of 2-methoxyphenol (2 g, 16.1 mmol), N,N-dimethylaniline (1.95 g, 16.1 mmol), phosgene (8.34 mL of a 1.93 M solution in toluene, 16.1 mmol) and a catalytic amount of DMF in chlorobenzene (5 mL) was stirred in a pressure tube for 2 h at 80° C. The organic layer was separated and concentrated in vacuo. The residue was distilled (Buchi Kugelrohr; bp=115° C. @ 10 mm Hg) to provide 2-methoxyphenyl chloroformate (1.5g; 50%) as a clear oil.

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated in vacuo
  3. distillationThe residue was distilled (Buchi Kugelrohr; bp=115° C. @ 10 mm Hg)

Sources & evidence

ORD record
ord-d441d990f8a04c2088accbd3027bf473
Source dataset
uspto-grants-2006_08
Patent number
US07084162B2

Linked notes

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