Carbon Disulfide → HCID 178455738, compound

HRID 249210Notes

Reaction equation

HRID 249210 reaction equation
[C:1]1([CH2:7][CH2:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][CH3:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1(=[O:23])[O:22][C:20](=[O:21])[CH2:19][CH2:18]1.C(=S)=S.[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[CH2:15]([C@H:12]1[CH2:13][CH2:14][C@H:9]([CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][C:4]([C:17]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:23])=[CH:3][CH:2]=2)[CH2:10][CH2:11]1)[CH3:16]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) ChlorideHCID 178455737HCID 178455737, compound

Product 1

HCID 178455738HCID 178455738, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-phenyl-2-(trans-4-ethylcyclohexyl)ethane (200.0 g, 0.93 mol), pulverized succinic acid anhydride (111.6 g, 1.11 mol) and CS2 (500 ml) was cooled with ice down to 0° to 5° C. Pulverized anhydrous aluminum chloride (248.0 g, 1.86 mol) was gradually added to the mixture. After removing the ice bath, the mixture was agitated for one hour and successively agitated for 2 hours on a water bath at 60° C. The resulting material was allowed to stand overnight. The reaction material was poured into a mixture of ice (500 g) and 6N-HCl (300 ml). The mixture was agitated sufficiently and CS2 and water were distilled off on a water bath, to obtain a residue. Toluene was added to the residue and then heated under reflux. After separating water by means of a DeanStoke type water separator, the resulting liquid was filtered off while hot and recrystallized to obtain the following 3-(4-(2-(trans-4-ethylcyclohexyl)ethyl)benzoyl)propanic acid (214 g, m.p.: 141.2°-142.6° C.). ##STR8##

Workup

  1. temperaturewas cooled with ice down to 0° to 5° C
  2. customAfter removing the ice bath
  3. stirringsuccessively agitated for 2 hours on a water bath at 60° C
  4. waitto stand overnight
  5. additionThe reaction material was poured into a mixture of ice (500 g) and 6N-HCl (300 ml)
  6. stirringThe mixture was agitated sufficiently
  7. distillationCS2 and water were distilled off on a water bath
  8. customto obtain a residue
  9. temperatureheated
  10. temperatureunder reflux
  11. customAfter separating water by means of a DeanStoke type water separator
  12. filtrationthe resulting liquid was filtered off while hot and
  13. customrecrystallized

Sources & evidence

ORD record
ord-f9babbfe4002489da777b4b233cf2a06
Source dataset
uspto-grants-1993_05
Patent number
US05213708

Reaction notes

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