Acrylonitrile → HCID 20383063, compound

HRID 1447791Notes

Reaction equation

HRID 1447791 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([OH:10])=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:11](#[N:14])[CH:12]=[CH2:13].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]2[O:10][CH2:13][CH:12]([C:11]#[N:14])[CH:5]([OH:6])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 7855Acrylonitrile2×HCID 124815-Chloro-salicylaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 20383063HCID 20383063, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred, refluxing mixture of 50 g of 3-chloro-6-hydroxybenzaldehyde and 62 ml of acrylonitrile in 50 ml of water was added dropwise over a three-hour period a solution of 12.8 g of sodium hydroxide in 120 ml of water. Then an additional 62 ml of acrylonitrile was added and the stirred mixture was refluxed for 2 hours, then allowed to stand at room temperature overnight. The crystals which formed were filtered off, washed with water and dried to give a solid, which was recrystallized from ethanol to give 6-chloro-3,4-dihydro-4-hydroxy-(2H)-1-benzopyran-3-carbonitrile (6A), a solid. A mixture of 6A with 250 ml of methanol containing 2 ml of sulfuric acid was refluxed for 4 days and stripped of solvent. The resulting residue was dry column chromatographed over silica gel, using Solvent No. 3 as eluent. The product obtained on workup was rechromatographed and recrystallized from ether to give methyl 6-chloro-2H-1-benzopyran-3-carboxylate (6B), as light yellow needles, mp: 106°-109° C.

Workup

  1. temperatureTo a stirred, refluxing
  2. temperaturethe stirred mixture was refluxed for 2 hours
  3. customThe crystals which formed
  4. filtrationwere filtered off
  5. washwashed with water
  6. customdried
  7. customto give a solid, which
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-e3ba1640e19e41c4ade7062e00de2348
Source dataset
uspto-grants-1979_12
Patent number
US04178380

Reaction notes

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