Acetone → 2,2-DIMETHYL-7-ETHOXY-6-METHOXY-4-CHROMANONE

HRID 1607647Notes

Reaction equation

HRID 1607647 reaction equation
[CH3:1]C(C)=O.C(=O)([O-])[O-].[K+].[K+].CI.[OH:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH2:25][CH3:26])[O:20][C:19]([CH3:28])([CH3:27])[CH2:18][C:17]2=[O:29]>>[CH3:1][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[O:24][CH2:25][CH3:26])[O:20][C:19]([CH3:28])([CH3:27])[CH2:18][C:17]2=[O:29]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14184037HCID 14184037, compound

Product 1

HCID 6881052,2-DIMETHYL-7-ETHOXY-6-METHOXY-4-CHROMANONEYield 92%

Conditions

Temperature
0 °C

Procedure

In 100 ml of acetone 4.7 g (20 millimoles) of 6-hydroxy-7-ethoxy-2,2-dimethyl-4-chromanone are dissolved, whereupon 4.1 g (30 millimoles) of potassium carbonate and 4.5 g (2 ml, 30 millimoles) of methyl iodide are added. The reaction mixture is refluxed for 4 hours, the inorganic salt is filtered off, washed twice with 20 ml of acetone and the half of the solvent is removed. The residue is cooled to 0° C., the precipitated product is filtered off and dried to constant weight. Thus 4.6 g of the desired compound are obtained, yield 92%. Mp.: 120°-122° C.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is refluxed for 4 hours
  3. filtrationthe inorganic salt is filtered off
  4. washwashed twice with 20 ml of acetone
  5. customthe half of the solvent is removed
  6. filtrationthe precipitated product is filtered off
  7. customdried to constant weight

Sources & evidence

ORD record
ord-08196adb939e4fd69bfd7cd790044d06
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

Loading…