Methyl chloroformate → HCID 21880821, compound

HRID 724467Notes

Reaction equation

HRID 724467 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].Cl[C:15]([O:17][CH3:18])=[O:16]>C(N(CC)CC)C>[C:15](=[O:16])([O:17][CH3:18])[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]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 728562,6-Di(prop-2-en-1-yl)phenol

Product 1

HCID 21880821HCID 21880821, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction was refluxed for 1 hr
  3. temperaturecooled
  4. additionpoured onto water
  5. washThe organic layer was washed with water (2×)
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-6e4bdb8596a546a59e66e30c5b7dec69
Source dataset
uspto-grants-2006_11
Patent number
US07141684B2

Reaction notes

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