Sulfuric Acid → HCID 20340180, compound

HRID 2049950Notes

Reaction equation

HRID 2049950 reaction equation
C(O[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:13])[CH3:12])(=O)C.[CH2:20]([CH:22]([CH2:26][CH2:27][CH2:28][CH3:29])[C:23]([OH:25])=[O:24])[CH3:21].S(=O)(=O)(O)O>>[CH2:20]([CH:22]([CH2:26][CH2:27][CH2:28][CH3:29])[C:23]([O:25][C:19]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:11]([C:6]1[CH:5]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:13])[CH3:12])=[O:24])[CH3:21]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 86972-Ethylhexanoic AcidHCID 12759835HCID 12759835, compound

Product 1

HCID 20340180HCID 20340180, compound

Procedure

Cumylphenyl 2-ethylhexanoate was prepared in accordance with the following procedure: a 2-liter flask equipped with a mechanical agitator, a ten theoretical plate fractionating column, an automatic reflux splitter pot, vapor thermo-controllers, a condenser, receivers, and external heating and cooling devices, was charged with 2 moles of cumylphenyl acetate, 5 moles of 2-ethylhexanoic acid and 5 grams of 98% sulfuric acid. Heat was supplied externally and the distillate was collected at a 20:1 reflux ratio at a vapor temperature below 120° C. at atmospheric pressure. A total of 64 cc of distillate was collected in 24 hours. The residual pot contents were cooled to ambient temperature and extracted 5 times with 2 l. of 8% sodium bicarbonate dried over anhydrous Na2SO4 and fractionated to give 408 g. (58 mole %) of a pale yellowish oil. The oil had a boiling point at 0.2 mm Hg of 252°-257° C., a specific gravity 20/20 of 1.045 and a saponification value of 2.82 meq/g. The cumylphenyl 2-ethylhexanoate ester has a theoretical saponification value of 2.85 meq/g.

Workup

  1. customa 2-liter flask equipped with a mechanical agitator
  2. temperaturea ten theoretical plate fractionating column, an automatic reflux splitter pot, vapor thermo-controllers, a condenser, receivers, and external heating
  3. temperaturecooling devices
  4. temperatureHeat
  5. distillationthe distillate was collected at a 20:1
  6. temperaturereflux ratio at a vapor temperature below 120° C. at atmospheric pressure
  7. distillationA total of 64 cc of distillate was collected in 24 hours
  8. extractionextracted 5 times with 2 l
  9. dry with materialof 8% sodium bicarbonate dried over anhydrous Na2SO4
  10. customto give 408 g
  11. customat 0.2 mm Hg of 252°-257° C.

Sources & evidence

ORD record
ord-6b5269eac7144991ba9430a48341ef94
Source dataset
uspto-grants-1980_04
Patent number
US04199517

Reaction notes

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