4-Hydroxybenzaldehyde → 4-{[4-(Acetyloxy)benzoyl]oxy}benzoic acid

HRID 1637304Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].OC1C=CC(C=O)=CC=1.C([O:26][C:27]1[CH:43]=[CH:42][C:30]([C:31]([O:33]C2C=CC(C=O)=CC=2)=[O:32])=[CH:29][CH:28]=1)(=O)C.[Mn]([O-])([O-])(=O)=O.[K+].[K+].Cl>C(O)(=O)C.C(OCC)(=O)C.C(C(C)=O)C>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:26][C:27]2[CH:43]=[CH:42][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=2)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

4-Acetoxybenzoyl chloride and 4-hydroxybenzaldehyde were used to prepare (4-formyl)phenyl 4-acetoxybenzoate, m.p. 98-100° C., in 45% yield. 18 g (0.063 mol) of this aldehyde were dissolved in 180 ml of glacial acetic acid, 9.5 g of potassium manganate and 180 ml of methyl ethyl ketone were added, and the mixture was heated to 50° C. with stirring. After 8 hours of stirring it was acidified with hydrochloric acid, 250 ml of ethyl acetate were added, and the phases were worked up. The concentrated ethyl acetate solution gave 16.8 g (89%) of 4-(4-acetoxybenzoyloxy)benzoic acid, C6H12O6 (300.3). The acid chloride was obtained in 95% yield from this acid by customary reaction with thionyl chloride.

Workup

stirringAfter 8 hours of stirring it
additionwere added

Sources & evidence

ORD record: ord-90e370cd169249ca8967ec140d941a92
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040411

Reaction notes

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