(3-Acetyloxy-5-carbonochloridoylphenyl) acetate → Benzaldehyde, 3,5-bis(acetyloxy)-

HRID 259189Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[C:8](Cl)=[O:9])(=[O:3])[CH3:2]>C1(C)C(C)=CC=CC=1.[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:14][C:15](=[O:17])[CH3:16])[CH:13]=1)[CH:8]=[O:9])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 61.8 g (0.24 mole) of 3,5-diacetoxybenzoyl chloride and 6 g of 5% palladium on BaSO4 in 200 ml of dry xylene was efficiently stirred while bubbling in hydrogen gas. The reaction mixture was slowly heated to 115° C. in an oil bath and the heating was continued until the evolution of HCl gas ceased (approximately 5 hours). After cooling, the mixture was filtered and the xylene was removed in vacuo to leave 48 g (90%) of 3,5-diacetoxybenzaldehyde which was used without further purification in subsequent reactions.

Workup

customwhile bubbling in hydrogen gas
custom(approximately 5 hours)
temperatureAfter cooling
filtrationthe mixture was filtered
customthe xylene was removed in vacuo

Sources & evidence

ORD record: ord-587d3ef3e4a5442186e125f7cccca717
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04036857

Reaction notes

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