Acetic Acid → HCID 20196231, compound

HRID 652705Notes

Reaction equation

HRID 652705 reaction equation
C(O)=O.[C:4]1([C:13]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]=1.[C:22](=[O:29])([O:26]CC)[O:23][CH2:24][CH3:25].C[O-].[Na+].C(O)(=O)C>O>[C:22](=[O:26])([O:23][CH2:24][CH3:25])[O:29][C:4]1([CH:13]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7766Diethyl CarbonateHCID 10942334Sodium MethoxideHCID 70441842HCID 70441842, compound

Product 1

HCID 20196231HCID 20196231, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 1 liter reaction vessel equipped with stirrer, thermometer and addition funnel are placed 339 grams (2.04 moles) of bicyclononenyl formate produced according to Example I containing compounds having the structures: ##STR175## 531 grams (4.5 moles) diethyl carbonate; and 31 grams (0.14 moles) of an aqueous 25% solution of sodium methoxide. The resulting mixture is stirred for a period of 1.25 hours. At the end of the 1.25 hour period, 30 grams (0.5 moles) of acetic acid and 2 liters of water is added to the reaction mass with stirring. The reaction mass is then washed with one 2 liter portion of saturated aqueous sodium chloride. The organic phase is then distilled on a 2" splash column yielding the following fractions:

Workup

  1. customInto a 1 liter reaction vessel
  2. customequipped with stirrer
  3. additionthermometer and addition funnel
  4. customproduced
  5. additioncontaining compounds
  6. stirringwith stirring
  7. washThe reaction mass is then washed with one 2 liter portion of saturated aqueous sodium chloride
  8. distillationThe organic phase is then distilled on a 2" splash column
  9. customyielding the following fractions

Sources & evidence

ORD record
ord-e874ed9fbcc9409493dc2c610e7799ce
Source dataset
uspto-grants-1987_06
Patent number
US04673533

Reaction notes

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