Jones' reagent → HCID 178443569, compound

HRID 247528Notes

Reaction equation

HRID 247528 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10](=[O:34])[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([C@H:20]3[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:22][CH2:21]3)=[O:19])=[CH:13][C:12]=2[Cl:33])=[CH:5][CH:4]=1)=[O:2].CC(C)=[O:37].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10](=[O:34])[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([C@H:20]3[CH2:25][CH2:24][C@H:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:22][CH2:21]3)=[O:19])=[CH:13][C:12]=2[Cl:33])=[CH:7][CH:8]=1)([OH:37])=[O:2]

Participants

4

Reactant 2

HCID 131709961Jones' reagentHCID 178443566HCID 178443566, compound

Product 1

HCID 178443569HCID 178443569, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The crude 2-chloro-4-{[(trans-4-heptylcyclohexyl)carbonyl]oxy}benzoic acid p-formylphenyl ester (19.1 g) obtained was dissolved in 800 ml of acetone. 30 ml of Jones' reagent were added dropwise to this solution within 15 minutes, the mixture warming slightly. The mixture was stirred for a further 40 minutes, then the separated inorganic material was filtered off under suction and the filtrate was concentrated. The residue was suspended in water and the suspension obtained was suction filtered. The residue was washed neutral with water on the suction filter and recrystallized from acetone, there being obtained 14.6 g of 2-chloro-4-{[(trans-4-heptylcyclohexyl)carbonyl]oxy}benzoic acid p-carboxyphenyl ester; m.p. (C-S) 135°-136° C., transition S-N 156° C., cl.p. (N-I) >300° C.

Workup

  1. temperaturethe mixture warming slightly
  2. filtrationthe separated inorganic material was filtered off under suction
  3. concentrationthe filtrate was concentrated
  4. customthe suspension obtained
  5. filtrationfiltered
  6. washThe residue was washed neutral with water on the suction
  7. filtrationfilter
  8. customrecrystallized from acetone, there

Sources & evidence

ORD record
ord-3f6e8bdba306407e83bcb1e2b2a586bd
Source dataset
uspto-grants-1987_11
Patent number
US04708441

Reaction notes

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