1-Naphthol → 1-Dichlorophosphoryloxynaphthalene

HRID 1508607Notes

Reaction equation

HRID 1508607 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[P:12](Cl)([Cl:15])([Cl:14])=[O:13].C(N(CC)CC)C>C(OCC)C>[P:12]([Cl:15])([Cl:14])([O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:13]

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 8471TriethylamineHCID 24813Phosphorus oxychloride

Product 1

HCID 5756311-DichlorophosphoryloxynaphthaleneYield 84.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared according to Standard Procedure A, from 1-naphthol (3.00 g, 20.81 mmol), phosphorus oxychloride (1.94 mL, 20.81 mmol), triethylamine (2.9 mL, 20.81 mmol) and anhydrous diethyl ether (70 mL). After 1 h at −78° C. the reaction was left to rise to room temperature and stirred for 3 h. The crude product was obtained as an oil. The resulting mixture was filtered and then evaporated in vacuo, after purification by column chromatography eluting with hexane-EtOAc, (1:1) to afford a colorless oil (4.59 g, 84%) [Rf=0.93 (hexane-EtOAc, 1:1)], 31P NMR (202 MHz, CDCl3): δP 5.07; 1H NMR (500 MHz, CDCl3): δH 7.52-7.71 (m, 4H, ArH), 7.86-7.89 (m, 1H, ArH), 7.95-7.98 (m, 1H, ArH), 8.16-8.19 (m, 1H, ArH).

Workup

  1. customPrepared
  2. customto rise to room temperature
  3. customThe crude product was obtained as an oil
  4. filtrationThe resulting mixture was filtered
  5. customevaporated in vacuo
  6. customafter purification by column chromatography
  7. washeluting with hexane-EtOAc, (1:1)

Sources & evidence

ORD record
ord-0868b019402b4b7db457db862c39934f
Source dataset
uspto-grants-2015_12
Patent number
US09221866B2

Reaction notes

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