p-Toluenesulfonic acid → HCID 5496199, compound

HRID 1241692Notes

Reaction equation

HRID 1241692 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=O.[CH2:12]([OH:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C1(C)C=CC(S(O)(=O)=[O:26])=CC=1>O>[Cl:11][C:9]1[CH:10]=[C:2]2[C:3](=[CH:7][CH:8]=1)[C:4](=[O:6])[C:17]1[C:12]([OH:18])=[CH:13][C:14]([OH:26])=[CH:15][C:16]=1[NH:1]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 81031-HexanolHCID 6930656HCID 6930656, compound

Product 1

HCID 5496199HCID 5496199, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Method E-5) 2-Amino-4-chlorobenzoate (50 g, 0.27 mol), dry phlorglucinol (40 g, 0.32 mol), hexanol (120 ml), and p-toluene sulphonic acid (1.6 g, 9 mmol) were mixed and heated to reflux with Dean-Stark removal of water for 2 hrs. On cooling petroleum ether (2 L) was slowly added and the solid was filtered off, washed with petroleum ether and dichloromethane to give the title compound (58.8 g, 0.22 mmol, 83.4%).

Workup

  1. additionwere mixed
  2. temperatureheated
  3. additionwas slowly added
  4. filtrationthe solid was filtered off
  5. washwashed with petroleum ether and dichloromethane

Sources & evidence

ORD record
ord-57749e8bc4e3486e9d9092268b9493d5
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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