Acrylonitrile → HCID 20383063, compound
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.C(O)C>[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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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 dissolved in ethanol. The solution was cooled and filtered to give 6-chloro-3,4-dihydro-4-hydroxy-(2H)- 1-benzopyran-3-carbonitrile (5A), a solid. A mixture of 5A 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 recrystallized from ether to give methyl 6-chloro-2H-1-benzopyran-3-carboxylate (5B), as light yellow needles, m.p.: 106°-109°.
Workup
- temperatureTo a stirred, refluxing
- temperaturethe stirred mixture was refluxed for 2 hours
- customThe crystals which formed
- filtrationwere filtered off
- washwashed with water
- customdried
- customto give a solid, which
- temperatureThe solution was cooled
- filtrationfiltered
Sources & evidence
- ORD record
- ord-9eaa5f32f9a04c779b444daf7f6ff103
- Source dataset
- uspto-grants-1978_07
- Patent number
- US04103021
Reaction notes
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