Sulfuric Acid → HCID 86735403, compound

HRID 1834816Notes

Reaction equation

HRID 1834816 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)O.[CH3:15][C:16]1[CH:21]=C(C(C)(C)C)C(O)=[C:18](C(C)(C)C)[CH:17]=1.CC(=C)CCO>O.C1CCCCC1>[CH3:2][C:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:15][CH:16]([CH3:21])[CH:17]=[CH:18][O:3]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7410AcetophenoneHCID 129883-Methyl-3-buten-1-olHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 86735403HCID 86735403, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
94 °C

Procedure

Into a 1-liter three neck flask equipped with stirrer, condenser, Barrett Trap, thermometer, addition funnel and heating mantle is placed 288 gms (2.4 moles) of acetophenone, 150 ml cyclohexane, 1 g of concentrated sulfuric acid and 1 g of Ionol® . The resulting mixture is heated to reflux temperature (94° C). Then 208 gms (2.4 moles) of 3-methyl-3-buten-1-ol is added, dropwise from the addition funnel, to the reaction mass with stirring while maintaining the reaction mass at reflux. Water of reaction formed is azeotroped over into the Barrett Trap. The reaction mass is heated for a period of 10 hours, during which time 24 ml water collected. At the end of the 10 hour period, the reaction is cooled to room temperature and 2 gms of a 50% sodium hydroxide solution are added. The reaction mass is then rushed over using a 2 inches splash column after adding thereto 10 gms Primol® and 0.1 gms Ionol®. Fractions collected and fractionation data for this rush over is as follows:

Workup

  1. additionBarrett Trap, thermometer, addition funnel
  2. temperatureheating mantle
  3. temperatureThe resulting mixture is heated
  4. temperaturewhile maintaining the reaction mass
  5. temperatureat reflux
  6. customformed
  7. customis azeotroped over into the Barrett Trap
  8. temperatureThe reaction mass is heated for a period of 10 hours, during which time 24 ml water
  9. customcollected
  10. temperatureAt the end of the 10 hour period, the reaction is cooled to room temperature
  11. addition2 gms of a 50% sodium hydroxide solution are added
  12. additionafter adding
  13. customFractions collected

Sources & evidence

ORD record
ord-56f3e08a47d44ab3a69657dc2afa4691
Source dataset
uspto-grants-1978_01
Patent number
US04071535

Reaction notes

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