Phosgene → 2,2-Diphenyl-ethyl chloroformate

HRID 981457

Reaction equation

HRID 981457 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16](Cl)([Cl:18])=[O:17]>C1(C)C=CC=CC=1>[Cl:18][C:16]([O:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:17]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 74662beta-Phenylphenethyl alcohol

Product 1

HCID 145702852,2-Diphenyl-ethyl chloroformateYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 7.0 g (35.4 mmol) of the alcohol (12) in 50 mL toluene at 0 degrees C., was slowly added 100 mL phosgene in toluene (12.5% phosgene in toluene). The reaction mixture was stirred at 0 degrees C. for 30 minutes and then at room temperature for 2 hours. The excess reagent and solvent was removed under reduced pressure and the crude product was quickly passed through a pad of silica gel (silica gel, CH2Cl2 -Hexane 2:3) to yield 7.8 g (80%) of the chloroformate (13). DCI-NH3 -MS, m/z (relative intensity), 259 (M+, 55); 1H-NMR (CDCl3, 300 MHz) 7.28 (m, 10H), 4.83 (d, 2H, J=7.5 Hz), and 4.45 (t, 1H, J=7.5 Hz).

Workup

  1. customat 0 degrees C
  2. waitat room temperature for 2 hours
  3. customThe excess reagent and solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2125e313bbfe4d96827510293cbd4ef9
Source dataset
uspto-grants-1991_02
Patent number
US04992421

Linked notes

Loading…