p-Toluenesulfonic acid → HCID 56619410, compound

HRID 1156069Notes

Reaction equation

HRID 1156069 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6](=[O:15])[CH2:7][CH2:8][CH:9](O)[C:10]([Cl:13])([Cl:12])[Cl:11])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6](=[O:15])[CH2:7][CH:8]=[CH:9][C:10]([Cl:12])([Cl:13])[Cl:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 521998p-Toluenesulfonic acid monohydrateHCID 20536710HCID 20536710, compound

Product 1

HCID 56619410HCID 56619410, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-p-Chlorophenacyl-2-hydroxy-3,3,3-trichloropropane (450 mg) was dissolved in benzene and p-toluene sulphonic acid monohydrate (40 mg) added. The solution was refluxed with a Dean and Stark apparatus and any reaction followed by tlc. After 5 hours refluxing tlc revealed that only starting material was present. The solution was treated with a second portion of p-toluene sulphonic acid (100 mg) and further refluxed for 5 hours. The solution was allowed to stand over 60 hours and evaporated to dryness. tlc Analysis (10% Et.AC./petrol) revealed a new product (Rf 0.8) with no starting material remaining. The solution was taken up in ethyl acetate and passed down a short alumina column (to remove pTSA). Elution with 25% Et.Ac./petrol yielded the product. Yield 200 mg.

Workup

  1. temperatureThe solution was refluxed with a Dean and Stark apparatus
  2. temperatureAfter 5 hours refluxing tlc
  3. temperaturefurther refluxed for 5 hours
  4. customevaporated to dryness
  5. custompassed down a short alumina column (to remove pTSA)
  6. washElution with 25% Et
  7. custom/petrol yielded the product

Sources & evidence

ORD record
ord-0403bbdf52e24f6391ebbe8cd72322d0
Source dataset
uspto-grants-1982_06
Patent number
US04333952

Reaction notes

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