4-[acetyloxy-methyl]benzaldehyde → 4-(Acetoxymethyl)benzoic acid

HRID 2086325Notes

Reaction equation

HRID 2086325 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].CC(C)=[O:16].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]([O:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]([OH:16])=[O:11])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 5395854-[acetyloxy-methyl]benzaldehydeHCID 131709961Jones' reagent

Product 1

HCID 70215904-(Acetoxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-[acetyloxy-methyl]benzaldehyde (15.3 g, 86.5 mmol) in acetone (250 ml) was then reacted with Jones reagent (33.0 ml, a three-fold excess) while stirring (exothermal reaction). This was stirred for 2 h before filtering out the green solid. The green solid was then dried under reduced pressure and dissolved in ethyl acetate (400 ml) and washed with sodium carbonate solution and water until neutral. After removal of solvent, a crop of yellow crystals (13.3 g) was obtained which was then recrystallised in chloroform-hexane to give a white crystal (3) (12.62 g, 76%). m.p. 120-123° C.; Rf 0.29 (1:1 Hexane-ether v/v).

Workup

  1. custom(exothermal reaction)
  2. stirringThis was stirred for 2 h
  3. filtrationbefore filtering out the green solid
  4. customThe green solid was then dried under reduced pressure
  5. dissolutiondissolved in ethyl acetate (400 ml)
  6. washwashed with sodium carbonate solution and water until neutral
  7. customAfter removal of solvent

Sources & evidence

ORD record
ord-a91cc8b431de466083e385ec6a3db9f1
Source dataset
uspto-grants-2004_04
Patent number
US06723811B1

Reaction notes

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