Phenol → Phosphorodichloridic acid, phenyl ester

HRID 408968Notes

Reaction equation

HRID 408968 reaction equation
[P:1]([Cl:5])(Cl)([Cl:3])=[O:2].[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>C(OCC)C>[P:1]([Cl:5])([Cl:3])(=[O:2])[O:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 8471TriethylamineHCID 24813Phosphorus oxychloride

Product 1

HCID 13038Phosphorodichloridic acid, phenyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phosphorus oxychloride (3.23 mL, 1 equiv) and phenol (g, 1 equiv) were stirred in anhydrous diethyl ether (25 mL). Anhydrous triethylamine was added (4.84 mL, 1 equiv) at −78° C. and the solution was allowed to warm to room temperature after 25 min. The triethylamine hydrochloride salt was filtered off and the solvent was removed under reduced pressure to give a clear pale yellow oil (g, %). (oil solidified in the freezer).

Workup

  1. filtrationThe triethylamine hydrochloride salt was filtered off
  2. customthe solvent was removed under reduced pressure
  3. customto give a clear pale yellow oil (g, %)

Sources & evidence

ORD record
ord-4669715121734427b9850eddb53e9f5d
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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