Acetic Acid → HCID 13851038, compound

HRID 986757Notes

Reaction equation

HRID 986757 reaction equation
Br[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]=[C:11]([C:14]#[N:15])[C:10](=[O:16])[C:9]=2[CH:17]=1)([CH3:4])[CH3:3].C(O)(=O)C>O>[C:2]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH:12]=[C:11]([C:14]#[N:15])[C:10](=[O:16])[C:9]=2[CH:17]=1)([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13728613HCID 13728613, compound

Product 1

HCID 13851038HCID 13851038, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(1-bromo-1-methylethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile (2.0 g), acetic acid (20 ml) and water (5 ml) was heated at 100° C. for one hour, which was then concentrated. The concentrate was subjected to a silica-gel (100 g) column-chromatography, eluting with chloroform-acetone-formic acid (20:1:0.1). The initial eluate was recrystallized from ethanol to give colorless crystals (600 mg) of 6-isopropenyl-4-oxo-4H-1-benzopyran-3-carbonitrile, m.p. 142°-144° C.

Workup

  1. concentrationwhich was then concentrated
  2. washeluting with chloroform-acetone-formic acid (20:1:0.1)
  3. customThe initial eluate was recrystallized from ethanol

Sources & evidence

ORD record
ord-1c90cc9a38c94a28aa37625e0665a17b
Source dataset
uspto-grants-1987_12
Patent number
US04716167

Reaction notes

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