Water → 3-(Carboxymethyl)-2-chlorobenzoic acid

HRID 446371Notes

Reaction equation

HRID 446371 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[C:15]([CH2:16][C:17]#N)=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[OH2:19]>>[C:17]([CH2:16][C:15]1[C:7]([Cl:6])=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])([OH:2])=[O:19]

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 579893812-Chloro-3-(cyanomethyl)benzoic acid2×

Product 1

HCID 579889673-(Carboxymethyl)-2-chlorobenzoic acid

Conditions

Temperature
165 °C

Procedure

Concentrated sulfuric acid (60 mL) was added dropwise to ice-cold water (75 mL) and the resulting solution was added to 2-chloro-3-(cyanomethyl)benzoic acid [Aromatic Intermediate 11, step b] (14 g). The resulting suspension was heated to reflux (165° C.) for 30 min during which the starting material dissolved and a new precipitate was observed. The reaction was allowed to cool and was diluted with water (250 mL) and extracted with ethyl acetate (3×500 mL). The combined organic phases were washed with water (250 mL) and brine (250 mL), then dried over magnesium sulphate and evaporated to give the subtitled compound as a white solid. Yield 13.7 g.

Workup

  1. temperatureThe resulting suspension was heated
  2. dissolutiondissolved
  3. temperatureto cool
  4. extractionextracted with ethyl acetate (3×500 mL)
  5. washThe combined organic phases were washed with water (250 mL) and brine (250 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-487fcd0bc32f4c4e9650d7cfc572624e
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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