Citric Acid → 2-(Cyanomethyl)-5-methylbenzoic acid

HRID 1783297Notes

Reaction equation

HRID 1783297 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[N:12]O)[C:8]2=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].C1(C)C=CC(S(Cl)(=O)=[O:23])=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[C:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:10][C:9]=1[C:8]([OH:11])=[O:23])#[N:12]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 587173366-Methyl-2-hydroxyimino-1-indanone

Product 1

HCID 230848102-(Cyanomethyl)-5-methylbenzoic acidYield 44.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

6-Methyl-2-hydroxyimino-1-indanone (37 g) and sodium hydroxide (19.7 g) were dissolved in water (287 mL), and p-toluenesulfonyl chloride (44.3 g) was added with stirring at 50° C. After the completion of the reaction, aqueous citric acid solution was added to acidify the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated. Ether was added to the precipitated crystals, and the crystals were collected by filtration to give 2-cyanomethyl-5-methylbenzoic acid (16.3 g).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. additionEther was added to the precipitated crystals
  7. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-8d701be4f7e5458e98f5a8f5e6b675b1
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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