Hydrochloric Acid → HCID 20304490, compound

HRID 1732687Notes

Reaction equation

HRID 1732687 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]([CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:6][CH:5]=1)([OH:3])=[O:2].[OH:20]O.Cl>[OH-].[Na+].O>[C:1]([C:4]1[CH:19]=[CH:18][C:7]([CH:8]2[O:20][CH:9]2[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 39957814-Carboxychalcone

Product 1

HCID 20304490HCID 20304490, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 18.9 g of 4-carboxybenzalacetophenone in 7.5 ml of 1 N sodium hydroxide solution and 225 ml of water was added 15 ml of 30% hydrogen peroxide. After cooling in an ice-water bath, 50 ml of 0.5 N sodium hydroxide was added dropwise over 5 min. The reaction mixture was stirred at room temperature for 31/4 hrs. and acidified to pH of 6.5 with 1 N hydrochloric acid. After stirring at room temperature for 1 hr., the solid was collected on a filter, washed with water and air-dried. Recrystallization from ethanol gave 11 g of 3-(4-carboxyphenyl)-1-phenyl-2,3-epoxy-1-propanone as colorless crystals, m.p. 170°-172° C. after drying at 80° C. under vacuum for 3 hrs.

Workup

  1. temperatureAfter cooling in an ice-water bath
  2. stirringAfter stirring at room temperature for 1 hr
  3. custom, the solid was collected on a filter
  4. washwashed with water
  5. customair-dried
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-73617d7dd37a4569ba4a8a3ce5782da3
Source dataset
uspto-grants-1980_12
Patent number
US04238589

Reaction notes

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