1-Naphthol → 1-Dichlorophosphoryloxynaphthalene

HRID 408959

Reaction equation

HRID 408959 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.C(N(CC)CC)C>C(OCC)C>[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

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 8471TriethylamineHCID 24813Phosphorus oxychloride

Product 1

HCID 5756311-DichlorophosphoryloxynaphthaleneYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phosphorus oxychloride (1.94 mL, 1 equiv) and α-naphthol (Aldrich, 3 g, 1 equiv) were stirred in anhydrous diethyl ether (20 mL). Anhydrous triethylamine was added (2.90 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 (4.88 g, 90%).

Workup

  1. filtrationThe triethylamine hydrochloride salt was filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-60fb9df45ea44f87932f011862e456c1
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Linked notes

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