4-Hydroxybenzaldehyde → Benzaldehyde, 4-(acetyloxy)-

HRID 1649112Notes

Reaction equation

HRID 1649112 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>N1C=CC=CC=1>[C:10]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 7918Acetic Anhydride

Product 1

HCID 70144Benzaldehyde, 4-(acetyloxy)-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Hydroxybenzaldehyde was acetylated with pyridine and acetic anhydride as in Example 12 to give 4-acetoxybenzaldehyde which was subjected to dehydration condensation with ethylene glycol to give 2-(4-acetoxyphenyl)-1,3-dioxolan. To a solution of 2-4-acetoxyphenyl)-1,3-dioxolan (13 g) in dichloromethane, bis(trimethylsilyl)-5-fluorouracil prepared as in Example 1 from 5-fluorouracil (10 g) was added followed by treating as in Example 10 to give 4.5 g of crystalline 1-[α-(2-hydroxyethoxy)-4-acetoxybenzyl]-5-fluorouracil.

Sources & evidence

ORD record
ord-6184d64b464649439e33dc6bde3859e1
Source dataset
uspto-grants-1983_11
Patent number
US04415573

Reaction notes

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