HCID 21285309, compound → HCID 21285327, compound

HRID 1462607Notes

Reaction equation

HRID 1462607 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11](=[O:25])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CC(C)=[O:28].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11](=[O:25])[C:12]2[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:16][CH:17]=2)[CH:7]=[CH:6][C:3]=1[C:4]([OH:28])=[O:5]

Participants

4

Reactant 2

HCID 21285309HCID 21285309, compoundHCID 131709961Jones' reagent

Product 1

HCID 21285327HCID 21285327, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The resulting, crude 2-chloro-4-[(p-heptylbenzoyl)oxy]benzaldehyde is dissolved in 350 ml of acetone. Within 40 minutes there are added dropwise thereto 30 ml of Jones' reagent, the mixture warming slightly. The mixture is stirred for a further 1 hour, precipitated inorganic material is then filtered off under suction, the filtrate is diluted with 300 ml of water (the product precipitating), concentrated on a rotary evaporator to about 300 ml and the suspension obtained is suction filtered. The suction filter material is washed three times with 50 ml of 10% aqueous acetone, dried and recrystallized from about 60 ml of benzene. There are obtained 13.8 g of 2-chloro-4-[(p-heptylbenzoyl)oxy]benzoic acid, m.p. 108° C. (nematic).

Workup

  1. additionWithin 40 minutes there are added dropwise
  2. customprecipitated inorganic material
  3. filtrationis then filtered off under suction
  4. additionthe filtrate is diluted with 300 ml of water (the product
  5. customprecipitating),
  6. concentrationconcentrated on a rotary evaporator to about 300 ml
  7. customthe suspension obtained
  8. filtrationThe suction filter material
  9. washis washed three times with 50 ml of 10% aqueous acetone
  10. customdried
  11. customrecrystallized from about 60 ml of benzene

Sources & evidence

ORD record
ord-4c615bcbdf7448a8aa0339f9c71e95e9
Source dataset
uspto-grants-1984_07
Patent number
US04460770

Reaction notes

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