Benzene → HCID 13656356, compound

HRID 979722Notes

Reaction equation

HRID 979722 reaction equation
C1C=CC=CC=1.[C:7]([C:11]1[CH:12]=[C:13]([OH:18])[CH:14]=[CH:15][C:16]=1[Cl:17])([CH3:10])([CH3:9])[CH3:8].[Cl:19][C:20](OC(Cl)(Cl)Cl)=[O:21].C(N(CC)CC)C>CCCCCC>[Cl:19][C:20]([O:18][C:13]1[CH:14]=[CH:15][C:16]([Cl:17])=[C:11]([C:7]([CH3:10])([CH3:8])[CH3:9])[CH:12]=1)=[O:21]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 8471TriethylamineHCID 10426DiphosgeneHCID 10910230HCID 10910230, compound

Product 1

HCID 13656356HCID 13656356, compoundYield 135.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Into 50 ml of benzene were dissolved 9.2 g of 3-tert-butyl-4-chlorophenol and 5.5 g of trichloromethyl chloroformate, and a solution obtained by dissolving 5.8 g of triethylamine into 20 ml of benzene was added dropwise thereto with stirring and cooling by ice. After completion of this dropwise addition, the mixture was subjected to stirring for 12 hours at room temperature. To the reaction mixture were added 70 ml of hexane, and precipitated crystal was separated by filtration. The filtrate was washed with water and a saturated aqueous solution of sodium chloride in this order, and was dried over anhydrous calcium chloride. Thereafter, solvent was distilled off. The residue was distilled under reduced pressure to give 9.32 g of 3-tert-butyl-4-chlorophenyl chloroformate having boiling point of 105°-108° C./1 mmHg, of which properties are as follows.

Workup

  1. customa solution obtained
  2. additionwas added dropwise
  3. temperaturecooling by ice
  4. additionAfter completion of this dropwise addition
  5. stirringto stirring for 12 hours at room temperature
  6. customprecipitated crystal
  7. customwas separated by filtration
  8. washThe filtrate was washed with water
  9. dry with materiala saturated aqueous solution of sodium chloride in this order, and was dried over anhydrous calcium chloride
  10. distillationThereafter, solvent was distilled off
  11. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-fd2589d8df3543cd933ac121e183c8a2
Source dataset
uspto-grants-1987_05
Patent number
US04668831

Reaction notes

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