Diethyl chlorophosphate → HCID 21880814, compound

HRID 724468Notes

Reaction equation

HRID 724468 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH:11]=[CH2:12])[C:5]=1[OH:13])[CH:2]=[CH2:3].[OH-].[Na+].[P:16](Cl)([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17]>C1(C)C=CC=CC=1>[P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])([O:13][C:5]1[C:4]([CH2:1][CH:2]=[CH2:3])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:10][CH:11]=[CH2:12])=[O:17]

Participants

5

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 14798Sodium HydroxideHCID 728562,6-Di(prop-2-en-1-yl)phenol

Product 1

HCID 21880814HCID 21880814, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,6-Diallylphenol (3.16 gm, 0.018 mol) was diluted with toluene(50 ml) and sodium hydroxide (0.72 gm, 0.018 mol) added to the solution. The reaction flask was equipped with a Dean and Stark apparatus and refluxed for 1 hr to remove water and to form an anhydrous solution of the phenate salt. After cooling, diethyl chlorophosphate, (3.45 gm) was added and the solution stirred overnight. Filtration of the solids and evaporation of the toluene gave 2,6-diallylphenyl diethyl phosphate. MS m/z 310. (M+ calcd for C16H23PO4=310). H NMR (300 MHz, CDCl3) d 1.30–1.45 (t, 6, CH3), 3.66–3.72 (d, 4, CH2), 4.20–4.49 (m, 4, OCH2), 5.15–5.30 (m, 4, CH2 vinyl), 5.90–6.16 (m, 2, CH vinyl), 7.20 7.30 (m, 3, aromatic). Oxidation of the product as described in Example 1 gave 2,6-(2,3-epoxypropyl)phenyl diethyl phosphate. MS m/z 342 (M+ calcd for C16H23PO6=342). H NMR (300 MHz, CDCl3) d 3.65 (t, 6, CH3), 2.55–2.65 (m, 2, CH2 epoxypropyl), 2.75–2.85 (m, 2, CH2 epoxypropyl), 2.90–3.30 (m, 4, CH2 epoxypropyl), 3.40–3.55 (m, 2, CH epoxypropyl), 4.10–4.35 (m, 4, OCH2), 7.05–7.25 (m, 1, aromatic), 7.40–7.60 (m, 2, aromatic).

Workup

  1. additionadded to the solution
  2. customThe reaction flask was equipped with a Dean and Stark apparatus
  3. temperaturerefluxed for 1 hr
  4. customto remove water
  5. customto form an anhydrous solution of the phenate salt
  6. temperatureAfter cooling
  7. filtrationFiltration of the solids and evaporation of the toluene

Sources & evidence

ORD record
ord-385c9bced8cb49a9bcdc92c57288ff7a
Source dataset
uspto-grants-2006_11
Patent number
US07141684B2

Reaction notes

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