Benzene → HCID 19850512, compound

HRID 1607476Notes

Reaction equation

HRID 1607476 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].[CH3:11][C:12](=O)[CH2:13][CH2:14][CH3:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(OCC)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[O:1][C:12]([CH3:11])([CH2:13][CH2:14][CH3:15])[O:10][C:3]=2[CH:4]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 78952-PentanoneHCID 5877661,2-Benzenediol, 4-methoxy-

Product 1

HCID 19850512HCID 19850512, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.35 mole (48.5 g) of 1,2-dihydroxy-4-methoxybenzene, 0.38 mole (32.7 g) of 2-pentanone and 1 g of p-toluenesulphonic acid are added to 350 ml of benzene. The mixture is heated under benzene reflux in order to remove the water formed. After 50 hours' heating, the reaction mixture is cooled and is then filtered through paper. After evaporation under reduced pressure, a brown oil is obtained and is dissolved in 500 ml of ethyl ether. After extraction with a solution of sodium carbonate in water in order to remove the unreacted 1,2-dihydroxy-4-methoxybenzene, the ethereal phase is dried with sodium sulphate. After evaporation of the ethyl ether under reduced pressure, the expected product is obtained and is employed as such in the following stage.

Workup

  1. temperatureThe mixture is heated under benzene
  2. temperaturereflux in order
  3. customto remove the water
  4. customformed
  5. temperatureAfter 50 hours' heating
  6. temperaturethe reaction mixture is cooled
  7. filtrationis then filtered through paper
  8. customAfter evaporation under reduced pressure
  9. customa brown oil is obtained
  10. extractionAfter extraction with a solution of sodium carbonate in water in order
  11. customto remove the unreacted 1,2-dihydroxy-4-methoxybenzene
  12. dry with materialthe ethereal phase is dried with sodium sulphate
  13. customAfter evaporation of the ethyl ether under reduced pressure

Sources & evidence

ORD record
ord-0424c2fdbc6447e482d22e64eb67f5e6
Source dataset
uspto-grants-1989_09
Patent number
US04865617

Reaction notes

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