Carbon Dioxide → Benzopyran

HRID 1030821Notes

Reaction equation

HRID 1030821 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1O.C(=O)=O>S([O-])([O-])(=O)=O.[Cu+2]>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH2:2]1

Participants

4

Reactant 2

HCID 280Carbon DioxideHCID 11171070Chroman-2-ol

Product 1

HCID 9211BenzopyranYield 89.3%

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Procedure

A solution was prepared by dissolving 10 g (0.054 mole) of 1-acetyl-2-naphthol, 6.6 g (0.06 mole) of norcamphor and 8.7 g (0.10 mole) of morpholine in 300 cc of toluene, and the solution was boiled for 5 hours and water was separated. After termination of the reaction. toluene was removed under reduced pressure, and the remaining chromanone compound was recrystallized from acetone, and the chromanon compound was dissolved in 200 cc of methanol and lithium aluminum hydride was added to the solution to form a chromanol compound. Then, 6.49 g of this chromanol compound was heated at 170° C. to 180° C. together with anhydrous copper sulfate in a carbon dioxide current for 10 minutes and the obtained brown viscous liquid was purified by the chromatography on silica gel to obtain 5.1 g of a chromene compound represented by the following formula: ##STR71##

Workup

  1. customthe obtained brown viscous liquid was purified by the chromatography on silica gel

Sources & evidence

ORD record
ord-9ff41293342b468dadff4e24b3d2c746
Source dataset
uspto-grants-1992_04
Patent number
US05106998

Reaction notes

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