Diethyl Carbonate → HCID 20437245, compound

HRID 434486Notes

Reaction equation

HRID 434486 reaction equation
C(=O)(O[CH2:6][CH3:7])OCC.C[O-].[Na+].[CH:12]([O:14][CH:15]1[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18][CH2:17][CH2:16]1)=[O:13]>O>[CH:12]([O:14][C:15]1([CH:7]2[CH2:6][CH2:18][CH2:17][CH2:16][CH2:15][CH2:22][CH2:21]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:13]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 3018951HCID 3018951, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 20437245HCID 20437245, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Into a 2 liter reaction flask equipped with heating mantle, stirrer, Bidwell water trap, reflux condenser, thermometer and nitrogen blanket apparatus is placed 1,000 ml (8.4 moles) of diethyl carbonate, and 25 grams (0.45 moles) of sodium methoxide. The resulting mixture is heated to 85° C. While maintaining the reaction mass at 85°-86° C. over a period of 1 hour, 695 grams (4.5 moles) of a composition containing a major proportion of 4-cyclooctenyl formate having the structure: ##STR78## and a minor proportion of bicyclooctanyl formate having the structure: ##STR79## produced according to Example I, is added while removing ethyl formate reaction product from the reaction mass using the Bidwell trap. At the end of the 1 hour period, the reaction mass is stirred at a temperature of 85°-86° C. for an additional 1 hour.

Workup

  1. customInto a 2 liter reaction flask
  2. customequipped
  3. temperaturereflux condenser
  4. temperatureWhile maintaining the reaction mass at 85°-86° C. over a period of 1 hour

Sources & evidence

ORD record
ord-f0493a9ae3e144aeb9575d5035a3a857
Source dataset
uspto-grants-1983_08
Patent number
US04397789

Reaction notes

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