Acetic Acid → Phenol, 4-(2,2-dichloroethenyl)-

HRID 482858Notes

Reaction equation

HRID 482858 reaction equation
O1CCCCC1O[C:8]1[CH:9]=[C:10]([CH:14](OC(=O)C)[C:15]([Cl:18])(Cl)[Cl:16])[CH:11]=[CH:12][CH:13]=1.C(O)(=[O:25])C>[Zn]>[Cl:16][C:15]([Cl:18])=[CH:14][C:10]1[CH:11]=[CH:12][C:13]([OH:25])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13324246HCID 13324246, compound

Product 1

HCID 5324901Phenol, 4-(2,2-dichloroethenyl)-

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

22 g (0.06 mole) of 3-(tetrahydropyranyloxy)-1-(2,2,2-trichloro-1-acetoxyethyl)-benzene were dissolved in 80 ml of glacial acetic acid, 4.6 g (0.07 mole) of zinc dust were added a little at a time, and the mixture was heated at 60°-70° C. for 3 hours. The mixture was cooled and filtered, after which it was introduced into 1.5 liters of water and extracted with ether. The extracts were combined, washed three times with NaHCO3 solution and water, dried end evaporated down, and the residue was taken up in toluene. The solution was filtered over silica gel, and 8.0 g of 4-dichlorovinylphenol were obtained as a wax-like product.

Workup

  1. temperaturethe mixture was heated at 60°-70° C. for 3 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. additionafter which it was introduced into 1.5 liters of water
  5. extractionextracted with ether
  6. washwashed three times with NaHCO3 solution and water
  7. customdried end
  8. customevaporated down
  9. filtrationThe solution was filtered over silica gel

Sources & evidence

ORD record
ord-1d50582121f442ecbe772e253b86d310
Source dataset
uspto-grants-1986_03
Patent number
US04576935

Reaction notes

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