1-Naphthol → 1-Dichlorophosphoryloxynaphthalene

HRID 1658652Notes

Reaction equation

HRID 1658652 reaction equation
[P:1]([Cl:5])(Cl)([Cl:3])=[O:2].[C:6]1([OH:16])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1>[P:1]([Cl:5])([Cl:3])(=[O:2])[O:16][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[P:1]([Cl:5])(=[O:2])([O:16][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[O:16][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 70051-NaphtholHCID 24813Phosphorus oxychloride

Product 2

HCID 5756311-DichlorophosphoryloxynaphthaleneYield 94.6%HCID 21528567HCID 21528567, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 113 g. phosphoryl chloride and 0.8 g. pyridine there is added 72 g. alpha-napthol over a one and 1-half hour period at a temperature of 100°C. The temperature is held at 105°-110°C. for one and one-half hours and stripped. Distillation affords 94.6 percent naphthyl phosphorodichloridate and 3.4 percent dinaphthyl phosphorochloridate.

Workup

  1. additionTo a mixture of 113 g
  2. customover a one and 1-half hour period
  3. customat a temperature of 100°C
  4. customis held at 105°-110°C. for one and one-half hours
  5. distillationDistillation

Sources & evidence

ORD record
ord-3056e66ca24e4fe98f7ed097cdd3359c
Source dataset
uspto-grants-1976_06
Patent number
US03965220

Reaction notes

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