Dibromomethane → HCID 12531628, compound

HRID 1073376Notes

Reaction equation

HRID 1073376 reaction equation
Br[CH2:2]Br.[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[OH:15])[O:11][C:10]([CH3:17])([CH3:16])[CH2:9][C:8]2=[O:18].[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[CH2:2]1[O:15][C:14]2[CH:13]=[C:12]3[C:7]([C:8](=[O:18])[CH2:9][C:10]([CH3:16])([CH3:17])[O:11]3)=[CH:6][C:5]=2[O:4]1

Participants

6

Reactant 3

HCID 3024DibromomethaneHCID 14798Sodium HydroxideHCID 126377192,2-Dimethyl-6,7-dihydroxy-4-chromanone

Product 1

HCID 12531628HCID 12531628, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 20 ml of water, 5.2 g (30 millimole) of dibromo-methane and 0.5 g (1 millimole) of Adogen 464 (Aldrich) is heated to boiling under vigorous stirring. A solution of 4.2 g (20 millimoles) of 6,7-dihydroxy-2,2-dimethyl-4-chromanone and 50 ml of a 5% sodium hydroxide solution is added dropwise within 2 hours and heated to boiling for a further hour. The mixture is diluted with 100 ml of water and extracted twice with 50 ml of chloroform each. The organic layer is washed twice with 50 ml of water, dried over sodium sulfate, the solvent is removed and the residue crystallized from hexane. Thus 3.6 g of the desired compound are obtained, yield 85%. Mp: 61°-62° C.

Workup

  1. temperatureis heated
  2. temperatureheated
  3. waitto boiling for a further hour
  4. extractionextracted twice with 50 ml of chloroform each
  5. washThe organic layer is washed twice with 50 ml of water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed
  8. customthe residue crystallized from hexane

Sources & evidence

ORD record
ord-9e09be5c8e5048858f9ac5066d538e4b
Source dataset
uspto-grants-1990_11
Patent number
US04968819

Reaction notes

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