Benzene → HCID 21499160, compound

HRID 1730111Notes

Reaction equation

HRID 1730111 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(Cl)(=[O:16])CCCCC.[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[OH:9][CH:4]([CH2:5][CH:6]([Cl:8])[CH2:7][CH2:2][Cl:1])[C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]

Participants

5

Reactant 3

HCID 241Benzene2×HCID 115713,5-DichlorophenolHCID 67340Hexanoyl chloride

Product 1

HCID 21499160HCID 21499160, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

An amount of 163.0 g of 3,5-dichlorophenol is dissolved in 200 ml of benzene and 79.1 g of anhydrous pyridine; there is then added dropwise at 5°-15° C with stirring, in the course of 1 hour, a solution of 134.6 g of caproic acid chloride in 200 ml of benzene. The temperature of the reaction mixture is allowed to rise to 20° C; the precipitated pyridine hydrochloride is filtered off, the benzene solution washed with water and, after drying over sodium sulphate, completely concentrated in a water-jet vacuum. The caproic acid-3,5-dichlorophenyl ester remaining (255 g) is heated to 60° C, and an addition then made to it at this temperature in the course of 10 minutes, with stirring, of 400 g of anhydrous aluminium chloride. After 5 hours, the liquid reaction mixture is poured, as stirring is maintained, into 3 liters of ice water. The initially oily precipitate fully crystallises during subsequent stirring. It is filtered off, washed with water and dried in vacuo to obtain 210.7 g of 2-hydroxy-4,6-dichlorocaprophenone, M.P. 39°-41° C.

Workup

  1. additionthere is then added dropwise at 5°-15° C
  2. customto rise to 20° C
  3. filtrationthe precipitated pyridine hydrochloride is filtered off
  4. washthe benzene solution washed with water
  5. dry with materialafter drying over sodium sulphate
  6. concentrationcompletely concentrated in a water-jet vacuum
  7. additionan addition
  8. customthen made to it at this temperature in the course of 10 minutes
  9. stirringwith stirring, of 400 g of anhydrous aluminium chloride
  10. waitAfter 5 hours
  11. customthe liquid reaction mixture
  12. additionis poured
  13. stirringas stirring
  14. customThe initially oily precipitate fully crystallises during subsequent stirring
  15. filtrationIt is filtered off
  16. washwashed with water
  17. customdried in vacuo

Sources & evidence

ORD record
ord-1116e0424c604199b0679d580a783654
Source dataset
uspto-grants-1976_11
Patent number
US03991124

Reaction notes

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