p-Toluenesulfonic acid → HCID 10881050, compound

HRID 1274064Notes

Reaction equation

HRID 1274064 reaction equation
[Cl:1][C:2]1[C:14]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[OH:16])=[C:13]([Cl:23])[CH:12]=[CH:11][C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[C:14]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[OH:16])=[C:13]([Cl:23])[CH:12]=[CH:11][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10926273HCID 10926273, compound

Product 1

HCID 10881050HCID 10881050, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3.5 g (9.9 mmol) of tert-butyl 2,4-dichloro-3-((2-pyridyl)(hydroxymethyl))benzoate in 120 ml of toluene and 60 ml of water together with 1.9 g of p-toluenesulfonic acid are heated under reflux for 9 h. After cooling, the organic phase is separated off and the aqueous phase is admixed with a solution of 23.8 g of sodium dihydrogen phosphate in 280 ml of water and extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 1.9 g; 1H NMR, δ [ppm], (DMSO-d6): 6.5 (m), 7.2 (m), 7.5 (d), 7.6 (d), 7.95 (m), 8.4 (d), 13.5 (broad s)

Workup

  1. temperatureunder reflux for 9 h
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-2146409c36b4424fa6acd7f6a245e418
Source dataset
uspto-grants-2000_12
Patent number
US06156702

Reaction notes

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