4-Toluenesulfonyl chloride → 2-Cyanomethyl-4-methoxy-benzoic acid

HRID 2100714Notes

Reaction equation

HRID 2100714 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[C:7](=[N:13]O)[CH2:6]2.C1(C)C=CC(S(Cl)(=O)=[O:22])=CC=1>[OH-].[Na+]>[C:7]([CH2:6][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:9]=1[C:8]([OH:12])=[O:22])#[N:13]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 6822331HCID 6822331, compound

Product 1

HCID 2956352-Cyanomethyl-4-methoxy-benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

5-Methoxy-indan-1,2-dione-2-oxime (22 g, 0.12 mol) was added to a solution of 230 ml 8% NaOH. The mixture was heated to 50° C., and then p-toluenesulfonyl chloride (30 g, 0.16 mol) was added in portions. The mixture was heated at 80° C. for 15 min. After cooled to room temperature, the precipitate was removed, and the filtrate was acidified with concentrated HCl to pH=3-4. The precipitate was collected and dried to give colorless solid (22 g, 100% yield). LC-MS: 192 (MH+)

Workup

  1. temperatureThe mixture was heated at 80° C. for 15 min
  2. temperatureAfter cooled to room temperature
  3. customthe precipitate was removed
  4. customThe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-4e08570cfc8447018401d51296ebf527
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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