Hydrochloric Acid → 6H-Benzo[e]naphth[2,1-c][1,2]oxaphosphorin, 6-chloro-

HRID 1599109Notes

Reaction equation

HRID 1599109 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[P:18](Cl)(Cl)[Cl:19].Cl>[Cl-].[Zn+2].[Cl-]>[Cl:19][P:18]1[C:2]2[CH:3]=[CH:4][C:5]3[C:10]([C:1]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17]1)=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24387Phosphorus trichlorideHCID 11020410Phenol, 2-(1-naphthalenyl)-

Product 1

HCID 111196436H-Benzo[e]naphth[2,1-c][1,2]oxaphosphorin, 6-chloro-Yield 66%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

60 g (0.273 mol) of o-naphthylphenol and 0.6 g of zinc chloride are heated to 200° C. while stirring. 46 g (0.335 mol) of phosphorus trichloride are then added dropwise over a period of 5 hours and the mixture is subsequently stirred further for 4 hours under reflux. The off-gas (HCl) eliminated is conducted away. The mixture is then cooled and the excess phosphorus trichloride is distilled off under reduced pressure. The residue is distilled at a bath temperature of from 200° to 225° C. and 0.2 mbar by means of a bulb tube. This gives 51 g of 6-chloro-6H-benzo[e]naphth[2,1-c][1,21]oxaphosphorin which solidify in crystalline form. This corresponds to a yield of 66% of theory.

Workup

  1. stirringthe mixture is subsequently stirred further for 4 hours
  2. temperatureunder reflux
  3. temperatureThe mixture is then cooled
  4. distillationthe excess phosphorus trichloride is distilled off under reduced pressure
  5. distillationThe residue is distilled at a bath temperature of from 200° to 225° C. and 0.2 mbar by means of a bulb tube

Sources & evidence

ORD record
ord-3809c7691ba1411db42cc22cd506fe17
Source dataset
uspto-grants-1998_04
Patent number
US05739372

Reaction notes

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