Dimethylformamide → HCID 14184049, compound

HRID 1607626Notes

Reaction equation

HRID 1607626 reaction equation
CN(C)[CH:3]=[O:4].[C:6](=[O:9])([O-])[O-].[Na+].[Na+].S(OC)(O[CH3:16])(=O)=O.[OH:19][C:20]1[C:29](O)=[C:28]2[C:23](C(=O)[CH2:25][C:26]([CH3:32])([CH3:31])[O:27]2)=[CH:22][CH:21]=1>>[CH3:16][O:19][C:20]1[C:29]([O:9][CH3:6])=[C:28]2[C:23]([C:3](=[O:4])[CH2:25][C:26]([CH3:32])([CH3:31])[O:27]2)=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 14184035HCID 14184035, compound

Product 1

HCID 14184049HCID 14184049, compoundYield 84.6%

Procedure

In 50 ml of N,N-dimethyl-formamide 4.2 g (20 millimoles) of 7,8-dihydroxy-2,2-dimethyl-4-chromanone are dissolved and to the solution 6.4 g (60 millimoles) of sodium carbonate and 5.3 g (3.9 ml 42 millimoles) of dimethyl sulfate are added under stirring. The reaction mixture is stirred at 120° C. for 5 hours, poured onto 150 g of crushed ice and extracted three times with 50 ml of chloroform each. The organic phase is washed three times with 100 ml of water each, dried over sodium sulfate and the solvent is distilled off. The residue is crystallized from 75% methanol. Thus 4.0 g of the desired compound are obtained, yield 84.6%. Mp.: 75°-76° C.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred at 120° C. for 5 hours
  3. extractionextracted three times with 50 ml of chloroform each
  4. washThe organic phase is washed three times with 100 ml of water each,
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent is distilled off
  7. customThe residue is crystallized from 75% methanol

Sources & evidence

ORD record
ord-1bfc127b537f47f986f826f92bc42452
Source dataset
uspto-grants-1989_09
Patent number
US04866089

Reaction notes

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