Diethyl chlorophosphate → HCID 21880814, compound

Participants

Reaction Steps

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).

Provenance & Evidence