Hydrochloric Acid → 6-(1-Hydroxyethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile

HRID 2083229Notes

Reaction equation

HRID 2083229 reaction equation
C([O:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH:14]=[C:13]([C:16]#[N:17])[C:12](=[O:18])[C:11]=2[CH:19]=1)[CH3:6])(=O)C.[OH-].[Na+].Cl>>[OH:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH:14]=[C:13]([C:16]#[N:17])[C:12](=[O:18])[C:11]=2[CH:19]=1)[CH3:6]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 203582201-(3-Cyano-4-oxo-4H-1-benzopyran-6-yl)ethyl acetate

Product 1

HCID 136013256-(1-Hydroxyethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile

Procedure

A mixture of 1.43 parts of 6-(1-acetoxyethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile and 25 parts by volume of 1N-sodium hydroxide is stirred at room temperature for 80 minutes. After being acidified with 1N-hydrochloric acid, the reaction mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water and dried on Na2SO4. The ethyl acetate is distilled off and the resulting residue is recrystallized from ethyl acetate. The procedure yields 0.790 part of 6-(1-hydroxyethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile as colorless crystals. Melting point: 147°-148° C

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate
  2. washThe ethyl acetate layer is washed with water
  3. customdried on Na2SO4
  4. distillationThe ethyl acetate is distilled off
  5. customthe resulting residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c05b85cbfad3416685ecc796ca9bc821
Source dataset
uspto-grants-1978_04
Patent number
US04085116

Reaction notes

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