Hydrochloric Acid → HCID 14820106, compound

HRID 487077Notes

Reaction equation

HRID 487077 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(OCC)(=O)C>[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

7

Reactant 5

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

Product 1

HCID 14820106HCID 14820106, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.5 % of 3-[(4-acetyl-5-hydroxy-2-ethylphenoxy)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 ettracted with ethyl acetate. The organic layer was extracted with 1 N 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. extractionThe organic layer was extracted with 1 N sodium hydroxide
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c1796943aa24df595c48f1c914af799
Source dataset
uspto-grants-1994_03
Patent number
US05294613

Reaction notes

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