Water → 6-Hydroxy-7-isopropoxy-2,2-dimethyl-4-chromanone

HRID 1607640Notes

Reaction equation

HRID 1607640 reaction equation
CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH:12](I)([CH3:14])[CH3:13].O.[OH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[OH:28])[O:24][C:23]([CH3:30])([CH3:29])[CH2:22][C:21]2=[O:31]>>[OH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH:12]([CH3:14])[CH3:13])[O:24][C:23]([CH3:29])([CH3:30])[CH2:22][C:21]2=[O:31]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 126377192,2-Dimethyl-6,7-dihydroxy-4-chromanone

Product 1

HCID 143349716-Hydroxy-7-isopropoxy-2,2-dimethyl-4-chromanoneYield 90%

Conditions

Temperature
130 °C

Procedure

In 80 ml of N,N-dimethyl formamide 4.2 g (20 millimoles) of 6,7-dihydroxy-2,2-dimethyl-4-chromanone are dissolved, whereupon 4.1 g (30 millimoles) of potassium carbonate and 4.2 g (2.5 ml, 25 millimoles) of isopropyl iodide are added. The reaction mixture is heated at 130° C. for 6 hours, poured into 200 ml of water and extracted with 100 ml of carbon tetrachloride. To the aqueous layer 50 ml of an 5% sodium hydroxide solution are added and the mixture is cooled below 5° C. The mixture is acidified with concentrated hydrochloric acid, the precipitated crystalline substance is filtered off and crystallized from methanol. Thus 4.5 g of the desired compound are obtained, yield 90%, mp.: 138°-139° C.

Workup

  1. additionare added
  2. extractionextracted with 100 ml of carbon tetrachloride
  3. additionTo the aqueous layer 50 ml of an 5% sodium hydroxide solution are added
  4. temperaturethe mixture is cooled below 5° C
  5. filtrationthe precipitated crystalline substance is filtered off
  6. customcrystallized from methanol

Sources & evidence

ORD record
ord-2ff286c7e8f840eaa5d51ea46ec7d209
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

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