Hydroquinone → HCID 21520280, compound

HRID 1282834Notes

Reaction equation

HRID 1282834 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[Cl:8][C:9]1(Cl)[CH2:11][C:10]1([CH3:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C=CC(O)=CC=1)[OH:21].CCCCCC>C1C=CC=CC=1.O>[Cl:8][C:9]1[CH2:11][CH:2]([C:1]([OH:6])=[O:7])[CH:3]([C:4]([OH:21])=[O:5])[CH2:18][C:10]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 7923Maleic AnhydrideHCID 8058HexaneHCID 107129Benzene, (2,2-dichloro-1-methylcyclopropyl)-

Product 1

HCID 21520280HCID 21520280, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
197 °C

Procedure

Into a test tube fitted with a cold finger condenser and a nitrogen bypass was put maleic anhydride (1.93 g., 19.7 mmole) and 1,1-dichloro-2-methyl-2-phenylcyclopropane (4.06 g., 20.2 mmole) along with 17.6 mg. hydroquinone. The tube containing the mixture was partially immersed in an oil bath whose temperature was slowly increased. Initial gas evolution was noted at 160°C. (bath). Steady gas evolution occurred at 178°C. with a final heating to 197°C. to insure complete reaction. Total heating time was 6 hours. The product was dissolved in benzene (5 ml.) and the solution was poured into 50 ml. n-hexane. The resultant oil soon crystallized giving 4.65 g (90 percent, m.p. 82°-90°C.) crude product which behaved as a mixture of anhydride and acid. Solution in water gave pure 1-chloro-2-phenylcyclohexene-4,5-dicarboxylic acid (m.p. 187°-189°C.).

Workup

  1. customInto a test tube fitted with a cold finger condenser
  2. additionThe tube containing the mixture
  3. customwas partially immersed in an oil bath
  4. temperaturewhose temperature was slowly increased
  5. customwas noted at 160°C.
  6. customoccurred at 178°C.
  7. customreaction
  8. additionthe solution was poured into 50 ml
  9. customThe resultant oil soon crystallized
  10. customgiving 4.65 g (90 percent, m.p. 82°-90°C.) crude product which

Sources & evidence

ORD record
ord-c5b1d214b14f45a4b6f2a326bd3ae3c4
Source dataset
uspto-grants-1976_08
Patent number
US03972901

Reaction notes

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