Hydrochloric Acid → HCID 10248190, compound

HRID 1252553Notes

Reaction equation

HRID 1252553 reaction equation
[C:1]([O:10][C:11]1[C:12]([O:17][CH3:18])=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:19](O)(=[O:27])[C:20]1[C:21](=[CH:23][CH:24]=[CH:25][CH:26]=1)[OH:22].P(Cl)(Cl)(Cl)=O.Cl.[OH-].[Na+]>CN(C)C=O>[CH3:18][O:17][C:12]1[C:11]([O:10][C:1]([C:2]2[C:3]([O:4][C:19]([C:20]3[C:21]([OH:22])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:27])=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:9])=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 338Salicylic AcidHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 66596Guaiacol salicylate

Product 1

HCID 10248190HCID 10248190, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

244 g of guaiacol salicylate (1.0 mole) and 138 g of salicylic acid (1.0 mole) are suspended in 1 liter of dimethylformamide. 80 g of phosphorus oxychloride are added over a period of about one hour to the solution, which is kept heated under agitation to 60°-70° C., and the mixture is maintained at this temperature until hydrochloric acid ceases to be evolved. The homogeneous dense mass, of straw colour, is poured under energetic agitation into 5 liters of a water-ice mixture and the suspension is neutralised slowly with dilute sodium hydroxide. The crystalline white solid which precipitates is filtered off, washed abundantly with water and then crystallised from isopropanol to obtain an overall yield of 60%. The product has a melting point of 85°-86° C.

Workup

  1. temperatureis kept heated under agitation to 60°-70° C.
  2. customThe crystalline white solid which precipitates
  3. filtrationis filtered off
  4. washwashed abundantly with water
  5. customcrystallised from isopropanol
  6. customto obtain an overall yield of 60%

Sources & evidence

ORD record
ord-e9259f7af4c24c29b8c9386cdffdd0a4
Source dataset
uspto-grants-1988_05
Patent number
US04743704

Reaction notes

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