N,N-Dimethylaniline → 2,6-Di(propan-2-yl)phenyl carbonochloridate

HRID 1534160Notes

Reaction equation

HRID 1534160 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].[C:14](Cl)([Cl:16])=[O:15].CN(C)C1C=CC=CC=1>C1C=CC=CC=1>[Cl:16][C:14]([O:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11])=[O:15]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 4943PropofolHCID 6371Phosgene

Product 1

HCID 2716192,6-Di(propan-2-yl)phenyl carbonochloridate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

2,6-Diisopropylphenol (8.9 g; 0.05 mole) was dissolved in 35 mL benzene and cooled to -3° C. after which liquid phosgene (7.0 mL condensed at -70° C.) was added dropwise maintaining a temperature range of 0° to 3° C. N,N-dimethylaniline (6.0 g; 12.2 m mole) was added dropwise and stirred at 0° C. for 15 minutes. The yellow green suspension was quenched with 5 mL water and the layers were separated. The organic portion was washed with HCl (1N, 5 mL), saturated aqueous NaCl, dried over magnesium sulfate, filtered, and concentrated to dryness to give a green liquid which was distilled affording 2,6-diisopropylphenyl chloroformate as a yellow liquid. ##STR13##

Workup

  1. additionwas added dropwise
  2. temperaturemaintaining a temperature range of 0° to 3° C
  3. customThe yellow green suspension was quenched with 5 mL water
  4. customthe layers were separated
  5. washThe organic portion was washed with HCl (1N, 5 mL), saturated aqueous NaCl
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customto give a green liquid which
  10. distillationwas distilled

Sources & evidence

ORD record
ord-f1216b2b5a89445497381bb7244fea9d
Source dataset
uspto-grants-1992_02
Patent number
US05087726

Reaction notes

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