Dimethyl Sulfoxide → HCID 19850883, compound

HRID 1607645Notes

Reaction equation

CS(C)=O.C(=O)([O-])[O-:6].[K+].[K+].[I-].[K+].[CH:13](Br)([CH2:15][CH3:16])[CH3:14].O[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>[CH2:14]([O:6][CH:24]1[C:23](=[O:32])[C:22]2[C:27](=[C:28]([OH:29])[CH:19]=[CH:20][CH:21]=2)[O:26][C:25]1([CH3:31])[CH3:30])[CH2:13][CH2:15][CH3:16]

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 g (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 crystallised from 90% 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
customcrystallised from 90% ethanol

Sources & evidence

ORD record: ord-8881eeaa8ecb4725abcd5cce646bdab0
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04866089

Reaction notes

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