HCID 20159499, compound → HCID 21285333, compound

HRID 247519Notes

Reaction equation

HRID 247519 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CC(C)=[O:33].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:30])[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]([OH:33])=[O:5]

Participants

4

Reactant 2

HCID 20159499HCID 20159499, compoundHCID 131709961Jones' reagent

Product 1

HCID 21285333HCID 21285333, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The crude 2-chloro-4-{[p-(p-hexylphenyl)benzoyl]oxy}benzaldehyde (67.1 g) obtained was dissolved in 2500 ml of acetone. 80 ml of Jones' reagent were added dropwise to this solution within 45 minutes, the mixture warming slightly. The mixture was stirred for a further 3 hours, then the precipitated inorganic material was filtered off under suction and the acetone was distilled off on a rotary evaporator. The residue was suspended in water and the suspension was suction filtered. The crude 2-chloro-4-{[p-(p-hexylphenyl)benzoyl]oxy}benzoic acid obtained was washed neutral on the suction filter with water and then, for purification, boiled up with methanol, cooled, filtered off and dried. Yield 58.5 g; m.p. 163.8°-165.5° C.

Workup

  1. temperaturethe mixture warming slightly
  2. filtrationthe precipitated inorganic material was filtered off under suction
  3. distillationthe acetone was distilled off on a rotary evaporator
  4. filtrationsuction filtered

Sources & evidence

ORD record
ord-d6a8c9d12c5041e99c9549f7ee43e8af
Source dataset
uspto-grants-1987_11
Patent number
US04708441

Reaction notes

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