Methanol → 7-(2-Hydroxy-n-propoxy)-2,2-dimethyl-4-chromanone

HRID 1073382Notes

Reaction equation

HRID 1073382 reaction equation
CO.[OH-].[K+].[OH:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:18])[CH2:11][C:12]([CH3:17])([CH3:16])[O:13]2)=[CH:8][CH:7]=1.[CH2:19]1[O:22][CH:20]1[CH3:21]>O>[OH:22][CH:20]([CH3:21])[CH2:19][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:18])[CH2:11][C:12]([CH3:16])([CH3:17])[O:13]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6378Propylene OxideHCID 14797Potassium HydroxideHCID 6009027-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 221588287-(2-Hydroxy-n-propoxy)-2,2-dimethyl-4-chromanoneYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 40 ml of methanol, 5 ml of water 1.1 g (20 millimoles) of potassium hydroxide and 3.8 g (20 millimoles) of 7-hydroxy-2,2-dimethyl-4-chromanone under stirring 11.6 g (14 ml, 0.2 mole) of propene oxide are added and the reaction mixture is refluxed for 5 hours. The reaction mixture is diluted with 200 ml of water and worked up according to Example 12. Thus 4.0 g of the desired compound are obtained, yield 80%. Mp.: 111°-113° C.

Workup

  1. additionare added
  2. temperaturethe reaction mixture is refluxed for 5 hours

Sources & evidence

ORD record
ord-f365b0b9cb4646848ad6cc21a37e1e66
Source dataset
uspto-grants-1990_11
Patent number
US04968819

Reaction notes

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