Cumene → 7399-64-6

HRID 256486Notes

Reaction equation

HRID 256486 reaction equation
C1(C(C)C)C=CC=CC=1.[Na].C(O)(C1C=CC=CC=1)(C)C.[CH2:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:29]1([CH2:35][CH2:36][C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([CH3:39])[CH3:38])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO.O>[C:23]1([CH2:22][CH2:21][CH:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:36][C:37]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)([CH3:39])[CH3:38])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 5

HCID 7406Cumene2×HCID 7501StyreneHCID 120532-Phenyl-2-propanolHCID 2440151,1'-(3-Methylbutane-1,3-diyl)dibenzeneHCID 5360545Sodium2×

Product 1

HCID 2440217399-64-6

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
135 °C

Procedure

A one-liter glass flask equipped with a stirrer, a dropping funnel with a gas introduction conduit, a reflux with a calcium chloride tube, and a thermometer was charged with 240 grams (2.0 moles) of commercially available cumene saturated with water, 4.0 grams (0.17 mole) of metallic sodium, and 2.7 grams (0.02 mole) of cumyl alcohol while introducing argon gas through the gas introduction conduit, and the resulting mixture was heated to 135° C. A mixture of 69 grams (0.66 mole) of commercially available styrene saturated with water and 60 grams (0.50 mole) of commercially available cumene saturated with water was dropped thereto over 2 hours with stirring while maintaining the temperature of the reaction system at 135°-140° C. After dropwise addition was completed, the reaction mixture was further stirred while heating for 1 hour and then cooled to room temperature. An excess of metallic sodium was decomposed by dropping methanol in small portions while stirring. Introduction of argon gas was stopped, and the contents were transferred to a separating funnel and then washed with water. The aqueous layer was removed, and the remaining oily layer was analyzed by gas chromatography. This gas chromatographic analysis showed that 58.7 grams (0.26 mole) of 1,3-diphenyl-3-methylbutane and 36.9 grams (0.11 mole) of 1,3,5-triphenyl-5-methylhexane were formed. The total yield (per styrene) was 73 mole %.

Workup

  1. customA one-liter glass flask equipped with a stirrer, a dropping funnel with a gas introduction conduit
  2. temperaturea reflux with a calcium chloride tube
  3. additionwhile introducing argon gas through the gas introduction conduit
  4. additionwas dropped
  5. temperaturewhile maintaining the temperature of the reaction system at 135°-140° C
  6. additionAfter dropwise addition
  7. stirringthe reaction mixture was further stirred
  8. temperaturewhile heating for 1 hour
  9. temperaturecooled to room temperature
  10. stirringwhile stirring
  11. customthe contents were transferred to a separating funnel
  12. washwashed with water
  13. customThe aqueous layer was removed

Sources & evidence

ORD record
ord-ef1fdd21bdc444f7829b2af04482838c
Source dataset
uspto-grants-1987_10
Patent number
US04703124

Reaction notes

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