1-Propanol → 2-carbopropoxy-6-hydroxy-4-oxo-4H-1-benzopyran

HRID 1110899Notes

Reaction equation

HRID 1110899 reaction equation
[C:1]([C:4]1[O:5][C:6]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:7]=2[C:8](=[O:10])[CH:9]=1)([OH:3])=[O:2].[CH2:16](O)[CH2:17][CH3:18]>S(=O)(=O)(O)O>[C:1]([C:4]1[O:5][C:6]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:7]=2[C:8](=[O:10])[CH:9]=1)([O:3][CH2:16][CH2:17][CH3:18])=[O:2]

Participants

4

Reactant 2

HCID 10311-PropanolHCID 152253396-Hydroxy-4H-4-oxochromene-2-carboxylic acid

Product 1

HCID 199138472-carbopropoxy-6-hydroxy-4-oxo-4H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

14.14 g (49.2 mmoles) of 2-carboxy-6-hydroxy-4-oxo-4H-1-benzopyran is dissolved in 200 ml of n-propanol and 1 drop of concentrated sulfuric acid is added. The mixture is refluxed for 30 hours, concentrated. The resulting solid is suspended in water, neutralized with sodium bicarbonate and filtered, washing the solid with water, then drying. This gives 10.6 g of 2-carbopropoxy-6-hydroxy-4-oxo-4H-1-benzopyran as a solid which is purified by recrystallization from n-propanol/acetone or by HPLC.

Workup

  1. temperatureThe mixture is refluxed for 30 hours
  2. concentrationconcentrated
  3. filtrationfiltered
  4. washwashing the solid with water
  5. customdrying
  6. customThis gives 10.6 g of 2-carbopropoxy-6-hydroxy-4-oxo-4H-1-benzopyran as a solid which is purified by recrystallization from n-propanol/acetone or by HPLC

Sources & evidence

ORD record
ord-e0d75e8be2574821b8ab3955bc35e48b
Source dataset
uspto-grants-1990_12
Patent number
US04977162

Reaction notes

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