Ethanol → Acetic Anhydride

HRID 965019Notes

Reaction equation

HRID 965019 reaction equation
[CH:1]([C:4]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[C:11]2[C:5]=1[C:6](=[O:17])[NH:7][S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2].C=[O:19].[CH2:20]([OH:22])[CH3:21]>>[OH:22][CH2:20][N:7]1[C:6](=[O:17])[C:5]2[C:11](=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:4]=2[CH:1]([CH3:3])[CH3:2])[S:8]1(=[O:9])=[O:10].[C:20]([O:19][C:13](=[O:15])[CH3:14])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 702EthanolHCID 712FormaldehydeHCID 101473624-Isopropyl-6-methoxysaccharin

Product 2

HCID 7918Acetic AnhydrideHCID 700507902-Hydroxymethyl-4-isopropyl-6-methoxysaccharin

Procedure

Condensation of 4-isopropyl-6-methoxysaccharin with aqueous formaldehyde in ethanol gives 2-hydroxymethyl-4-isopropyl-6-methoxysaccharin, acetylation of which with acetic anhydride and a catalytic amount of sulfuric acid gives 2-acetoxymethyl-4-isopropyl-6-methoxysaccharin.

Sources & evidence

ORD record
ord-b9fdb1f2132f4d4a92ee1b63417e3b8d
Source dataset
uspto-grants-1998_06
Patent number
US05773456

Reaction notes

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