Benzoic Acid → Benzoyl chloride, 2-butoxy-6-nitro-

HRID 1681695Notes

Reaction equation

HRID 1681695 reaction equation
S(Cl)([Cl:3])=O.[C:5](O)(=O)[C:6]1C=CC=[CH:8][CH:7]=1.[OH-].[Na+].[OH:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:18]=1[C:19]([OH:21])=O.C(I)CCC.C(=O)([O-])[O-].[K+].[K+]>C(O)C.CN(C)C=O>[CH2:5]([O:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[C:18]=1[C:19]([Cl:3])=[O:21])[CH2:6][CH2:7][CH3:8]

Participants

9

Reactant 6

HCID 243Benzoic AcidHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 149439032-Hydroxy-6-nitrobenzoic acid

Product 1

HCID 19805532Benzoyl chloride, 2-butoxy-6-nitro-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

Ra=4-butoxy, Rb=H. 2-Butoxy-6-nitrobenzoyl chloride was prepared by the reaction of thionyl chloride and the corresponding benzoic acid which, in turn, was prepared by hydrolysis of the corresponding butyl ester with sodium hydroxide in aqueous ethanol. The butyl ester was prepared by heating together a mixture containing 2-hydroxy-6-nitrobenzoic acid (Chem.Abs., 1963, 59, 500 g), butyl iodide, potassium carbonate and N,N-dimethylformamide.

Workup

  1. temperatureby heating together a mixture

Sources & evidence

ORD record
ord-d9b757de6b7f473dae75346b1ca7aed6
Source dataset
uspto-grants-1992_12
Patent number
US05173496

Reaction notes

Loading…