Acetic Acid → Benzaldehyde, 4-(acetyloxy)-

HRID 1710217Notes

Reaction equation

C1(CC([O-])=O)C=CC(C)=CC=1.C(OC(=O)C)(=O)C.C(O)(=O)C.[Na+].[Br-].O=O.[C:27]([O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1)(=[O:29])[CH3:28]>>[C:27]([O:30][C:31]1[CH:39]=[CH:38][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1)(=[O:29])[CH3:28]

Participants

Reactant 6

HCID 176Acetic Acid

HCID 977Oxygen

HCID 7918Acetic Anhydride

HCID 16865Benzoic acid, 4-(acetyloxy)-

HCID 253881Sodium Bromide

HCID 7014866HCID 7014866, compound

Product 1

HCID 70144Benzaldehyde, 4-(acetyloxy)-

Conditions

Temperature: 100 °C

Procedure

Twenty (20) g. (0.13 moles) of p-cresylacetate, 40 g. (0.39 moles) of acetic anhydride, 40 g. (0.67 moles) of acetic acid, 0.5 g. (0.002 moles) Co(OAc)2· 4H2O, 0.49 g. (0.002 moles) Mn(OAc)2· 4H2O, and 0.43 g. (0.004 moles) NaBr were combined in a glass reactor and heated to 100° C. at atmospheric pressure under air flow of 50 ml/min. The reaction was continued for 71 hours at which time oxygen uptake ceased. Upon cooling, the reaction mixture solidified. Analysis of this material showed p-acetoxybenzoic acid in 77 mole percent yield and p-acetoxybenzaldehyde in 5 mole percent yield. No unreacted p-cresylacetate was detected. The low yield is believed to result from work-up procedures.

Workup

temperatureUpon cooling
customyield

Sources & evidence

ORD record: ord-da6258e303d14f54815c781333c3c9d9
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04952721

Reaction notes

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