Styrene → Styrene

HRID 246901

Reaction equation

HRID 246901 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].[CH2:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(C)C>[CH2:8]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C:7]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 7501StyreneHCID 13229CyclohexylbenzeneHCID 5360545Sodium

Product 3

HCID 7501StyreneHCID 13229CyclohexylbenzeneHCID 139816241-Phenyl-1-(2-phenylethyl)cyclohexane

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3,100 grams (g) of anhydrous phenylcyclohexane, 40 g of metallic sodium and 11 g of isopropyl alcohol was placed in a 5-liter glass flask and heated to 130° C., and 650 g of styrene was dropped over 3 hours while vigorously stirring and subsequently the resulting mixture was stirred for 1 hour to complete the reaction. Stirring was stopped and the reaction mixture was allowed to stand and cool. Then an oil layer was separated and 200 g of ethanol was added. The resulting mixture was washed three times with each of 2 liters (l) of a 5N aqueous solution of hydrochloric acid and 2 l of saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The unreacted phenylcyclohexane was distilled away by the use of a rotary evaporater, and the residue was distilled under reduced pressure to yield 850 g of a fraction having a boiling point of 160°-170° C. at 0.3 mmHg (this fraction is hereinafter referred to as "Fraction f-1") and 550 g of a fraction having a boiling point of 210°-220° C. at 0.3 mmHg (this fraction is hereinafter referred to as "Fraction f-2"). An analysis confirmed that the Fraction f-1 was a compound resulting from addition of one styrene molecule to phenylcyclohexane, i.e., 1-phenyl-1-(2-phenylethyl)cyclohexane, and the Fraction f-2 was a compound resulting from addition of two styrene molecules to phenylcyclohexane, i.e., 1-phenyl-1-(2,4-diphenylbutyl)cyclohexane.

Workup

  1. customwas placed in a 5-liter glass flask
  2. stirringsubsequently the resulting mixture was stirred for 1 hour
  3. customthe reaction
  4. stirringStirring
  5. temperaturecool
  6. customThen an oil layer was separated
  7. addition200 g of ethanol was added
  8. washThe resulting mixture was washed three times with each of 2 liters (l) of a 5N aqueous solution of hydrochloric acid and 2 l of saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe unreacted phenylcyclohexane was distilled away by the use of a rotary evaporater
  11. distillationthe residue was distilled under reduced pressure
  12. customto yield 850 g of a fraction

Sources & evidence

ORD record
ord-5842cbd05ef742fb9086b8b1fa9a345c
Source dataset
uspto-grants-1987_11
Patent number
US04704490

Linked notes

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