Beta-Alanine → HCID 135674613, compound

HRID 280276Notes

Reaction equation

HRID 280276 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([OH:17])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=O)[CH:7]=1.C[O-].[Na+].[NH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26].C1(C)C=CC=CC=1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([OH:17])=[C:6]([C:8](=[N:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 1140TolueneHCID 30211374',5-Dichloro-2-hydroxy-3-methylbenzophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 135674613HCID 135674613, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(5-Chloro-2-hydroxy-3-methylphenyl)-(4-chlorophenyl)-methanone (98.4 g, 0.35 mol), sodium methoxide (19 g, 0.35 mol) and β-alanine (31.2 g, 0.35 mol) are added to 2 liters of toluene and 0.5 liters of methanol. The mixture is heated gradually and the ternary azeotrope (62° C.) is distilled. After a Dean-Stark apparatus has been fitted, the residue is heated at the reflux temperature of toluene for 6 hours. The mixture is then evaporated to dryness in vacuo. The solid residue is triturated with diethyl ether and filtered off. The solid is dissolved in 1.5 liters of water. The aqueous solution is acidified by the addition of citric acid to pH 4. The solid obtained is filtered off and then dissolved in CHCl3. The chloroform solution is dried (MgSO4) and then evaporated in vacuo. The solid obtained is triturated in petroleum ether, filtered off and dried. This gives the desired acid product, melting at 137.5°-138° C.

Workup

  1. temperatureThe mixture is heated gradually
  2. distillationthe ternary azeotrope (62° C.) is distilled
  3. customAfter a Dean-Stark apparatus has been fitted
  4. temperaturethe residue is heated at the reflux temperature of toluene for 6 hours
  5. customThe mixture is then evaporated to dryness in vacuo
  6. customThe solid residue is triturated with diethyl ether
  7. filtrationfiltered off
  8. dissolutionThe solid is dissolved in 1.5 liters of water
  9. additionThe aqueous solution is acidified by the addition of citric acid to pH 4
  10. customThe solid obtained
  11. filtrationis filtered off
  12. dissolutiondissolved in CHCl3
  13. dry with materialThe chloroform solution is dried (MgSO4)
  14. customevaporated in vacuo
  15. customThe solid obtained
  16. customis triturated in petroleum ether
  17. filtrationfiltered off
  18. customdried

Sources & evidence

ORD record
ord-5d52b2e314184dd28ccb5cf3ad4f06f5
Source dataset
uspto-grants-1986_05
Patent number
US04588748

Reaction notes

Loading…