Malonic Acid → HCID 54131131, compound

HRID 1731156Notes

Reaction equation

HRID 1731156 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[C:9]([OH:17])=[C:10]([CH2:14][CH:15]=O)[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.C(O)(=O)[CH2:21][C:22]([OH:24])=[O:23]>>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[C:9]([OH:17])=[C:10]([CH2:14][CH:15]=[CH:21][C:22]([OH:24])=[O:23])[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 21495648HCID 21495648, compound

Product 1

HCID 54131131HCID 54131131, compound

Procedure

Another modification of the process comprises reacting 3-bromo-1-propene with methyl 2-hydroxybenzoate to obtain methyl 2'-(3-oxy-1-propene)-benzoate, hydrolyzing the latter to form the free acid, reacting the latter with a chlorinating agent such as thionyl chloride to form the corresponding acid chloride, condensing the latter with cadmium chlorophenyl to form 3-(2'-p-chlorobenzoyl-phenyl)oxy-1-propene, heating the latter to form 3-(3'-p-chlorobenzoyl-2'-hydroxy-phenyl)-1-propene, reacting the latter with an oxidizing atent to form 2-(3'-p-chlorobenzoyl-2'-hydroxy-phenyl)-1-oxo-ethane, condensing the latter with malonic acid, decarboxylating the resulting dicarboxylic acid to form 4-(3'-p-chlorobenzoyl-2'-hydroxy-phenyl)-2-butenoic acid and hydrogenating the latter in the presence of palladium to obtain 4-(3'-p-chlorobenzoyl-2-'-hydroxyphenyl)-butyric acid and finally with an oxidizing agent to form 4-(3'-p-chlorobenzoyl-2',5'-dihydroxy-phenyl)-butyric acid.

Workup

  1. customto form

Sources & evidence

ORD record
ord-2da9360f841f4fc1a50fc1d916be726b
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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