Phenyl phosphorus dichloride → O-(2,6-Di-tert-butyl-4-methylphenyl) phenylphosphonochloridite

HRID 224542

Reaction equation

HRID 224542 reaction equation
[C:1]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=[C:7]([CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:17][P:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(N(CC)CC)C>[C:19]1([P:18]([Cl:17])[O:11][C:10]2[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]([CH3:16])=[CH:8][C:9]=2[C:12]([CH3:15])([CH3:14])[CH3:13])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 12573Phenyl phosphorus dichlorideHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 53944288O-(2,6-Di-tert-butyl-4-methylphenyl) phenylphosphonochloridite

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 110 grams of 2,6-di-tert-butyl-p-cresol in 252 grams of triethylamine was added at 25°-26° C. over a 15-minute period 89.5 grams of dichlorophenylphosphine. The reaction mixture was heated for 31 hours at 95°-97° C. The excess triethylamine solvent was then removed by distillation under vacuum, the resulting residue was triturated with 200 ml of dry benzene, and the white crystalline solid triethylamine hydrochloride was separated by filtration. The desired product named above was isolated from the filtrate by distillation of the benzene under vacuum and crystallization of the residue from acetonitrile. The product was obtained as white crystals melting at 103°-106° C.

Workup

  1. temperatureThe reaction mixture was heated for 31 hours at 95°-97° C
  2. customThe excess triethylamine solvent was then removed by distillation under vacuum
  3. customthe resulting residue was triturated with 200 ml of dry benzene
  4. customthe white crystalline solid triethylamine hydrochloride was separated by filtration
  5. customabove was isolated from the filtrate by distillation of the benzene under vacuum and crystallization of the residue from acetonitrile

Sources & evidence

ORD record
ord-303f5b93ae484918862c034fb97dfa07
Source dataset
uspto-grants-1980_11
Patent number
US04233207

Linked notes

Loading…