Methyl chloroformate → HCID 21880821, compound

Participants

Reaction Steps

2,6-Diallylphenol (3.48, 0.02 mol) and triethylamine (4 ml) was diluted with 1,2-dichloromethane (50 ml). Methyl chloroformate (2.00 gm, 0.027 mol) was diluted with 1,2-dichloromethane (10 ml) and added drop wise to the phenol-amine solution. After the addition was complete, the reaction was refluxed for 1 hr, cooled and poured onto water. The organic layer was washed with water (2×) dried over MgSO4 and evaporated to give 2,6-diallylphenyl methyl carbonate. MS m/z 232 (M+ calcd for C15H16O3=232). H NMR (300 MHz, CDCl3) d 3.30–3.40 (d, 4. CH2), 3.90 (s, 3, CH3), 5.05–5.20 (m, 4, CH2 vinyl), 5.85–6.00 (m, 2, CH vinyl), 7.10–7.27 (m, 3, aromatic). Oxidation of the product as described in Example 1 gave 2,6-di(2,3-epoxypropyl)phenyl methyl carbonate as an oil. MS m/z 264 (M+ calcd for C14H16O5=264). H NMR (300 MHz, CDCl3) d 2.60–2.70 (m, 2, CH2 epoxypropyl), 2.40–2.90 (m, 6, CH2 epoxypropyl), 3.25–3.40 (m, 2, CH2 epoxypropyl), 3.85 (s, 3, OCH3), 7.30–7.65 (m, 3, aromatic).

Provenance & Evidence