Hydrochloric Acid → HCID 14820106, compound

HRID 2166386Notes

Reaction equation

HRID 2166386 reaction equation
[C:1]([C:4]1[C:19]([OH:20])=[CH:18][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#N)=[C:6]([CH2:21][CH3:22])[CH:5]=1)(=[O:3])[CH3:2].[OH-:23].[K+].C(O)C.Cl.[OH2:29]>>[C:1]([C:4]1[C:19]([OH:20])=[CH:18][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]([OH:29])=[O:23])=[C:6]([CH2:21][CH3:22])[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 14820097HCID 14820097, compound

Product 1

HCID 14820106HCID 14820106, compound

Procedure

A mixture of 1.5 g of 3-[(4-acetyl-5-hydroxy-2-ethyphenoxy)methyl]benzonitrile, 1.14 g of potassium hydroxide, 75 ml of ethanol and 75 ml of water was heated at reflux overnight. The mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was extracted with 1N sodium hydroxide. The base layer was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo providing 1.06 g of the desired title product, m.p.=161°-164° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate
  4. extractionThe organic layer was extracted with 1N sodium hydroxide
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea11c64c6b164c44b8f6486e9f92c47e
Source dataset
uspto-grants-1990_07
Patent number
US04945099

Reaction notes

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