Ethyl 2-hydroxyisobutyrate → Ethyl 2-(2-chloro-5-nitro-benzoyloxy)-2-methyl-propionate

HRID 2081147Notes

Reaction equation

HRID 2081147 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O[C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([O:6][C:15]([CH3:22])([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:5]

Participants

3

Reactant 2

HCID 6653Ethyl 2-hydroxyisobutyrateHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 19780825Ethyl 2-(2-chloro-5-nitro-benzoyloxy)-2-methyl-propionate

Procedure

Analogously to the procedure described in Example 74, from 2-chloro-5-nitro-benzoic acid via its acid chloride and ethyl α-hydroxy-isobutyrate there is obtained ethyl 2-(2-chloro-5-nitro-benzoyloxy)-2-methyl-propionate, m.p. 64°-66° C., which is subsequently reduced to ethyl 2-(5-amino-2-chloro-benzoyloxy)-2-methyl-propionate. B.p. 200°-230° C./0.1 torr;

Sources & evidence

ORD record
ord-afd8b0d01e3740448d9ac0229a4d03bc
Source dataset
uspto-grants-1993_02
Patent number
US05183492

Reaction notes

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