Dimethyl Sulfoxide → HCID 22158840, compound

HRID 1073389Notes

Reaction equation

CS(C)=O.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH:13](Br)([CH2:15][CH3:16])[CH3:14].[OH:18][C:19]1[C:28]([OH:29])=[C:27]2[C:22]([C:23](=[O:32])[CH2:24][C:25]([CH3:31])([CH3:30])[O:26]2)=[CH:21][CH:20]=1>COCCOCCOC>[CH:13]([O:18][C:19]1[C:28]([OH:29])=[C:27]2[C:22]([C:23](=[O:32])[CH2:24][C:25]([CH3:30])([CH3:31])[O:26]2)=[CH:21][CH:20]=1)([CH2:15][CH3:16])[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

In 80 ml of dimethyl sulfoxide 4.2 g (20 millimoles) of 7.8-dihydroxy-2,2-dimethyl-4-chromanone are dissolved, whereupon 10 ml of diethylene glycol dimethylether, 4.1 g (30 millimoles) of potassium carbonate, 0.5 g of potassium iodide and 3.3 (2.6 ml, 24 millimoles) of sec. butyl bromide are added. The reaction mixture is heated at 100° C. for 10 hours, poured onto 200 ml of crushed ice and extracted with 100 ml of carbon tetrachloride. To the aqueous phase 20 ml of 10% sodium hydroxide solution are added, the mixture is cooled to 0° C., acidified with concentrated hydrochloric acid and stirred at 0° C. for 2 hours. The product is filtered, washed twice with 20 ml of water, dried and crystallized from 20% ethanol. Thus 4.4. g of the desired compound are obtained, yield 83%, mp.: 108°-110° C.

Workup

additionare added
extractionextracted with 100 ml of carbon tetrachloride
additionTo the aqueous phase 20 ml of 10% sodium hydroxide solution are added
temperaturethe mixture is cooled to 0° C.
filtrationThe product is filtered
washwashed twice with 20 ml of water
customdried
customcrystallized from 20% ethanol

Sources & evidence

ORD record: ord-cd377231ba614649aff06c51317d0018
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04968819

Reaction notes

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