Acetic Anhydride → HCID 54335119, compound

HRID 2254254Notes

Reaction equation

HRID 2254254 reaction equation
[OH:1][C:2]1[C:21]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[C:20]([O:27][CH2:28][O:29][CH3:30])[CH:19]=[C:18]([O:31][CH2:32][O:33][CH3:34])[C:3]=1[C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][CH3:16])=[CH:9][CH:8]=1.[C:35](OC(=O)C)(=[O:37])[CH3:36].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:35]([O:1][C:2]1[C:21]([CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[C:20]([O:27][CH2:28][O:29][CH3:30])[CH:19]=[C:18]([O:31][CH2:32][O:33][CH3:34])[C:3]=1[C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][O:15][CH3:16])=[CH:9][CH:8]=1)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 54451455HCID 54451455, compound

Product 1

HCID 54335119HCID 54335119, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A liquid mixture of 13.75 g of the 2'-hydroxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone, 40 ml of acetic anhydride and 40 ml of anhydrous pyridine was stirred at room temperature to effect a reaction. Then, the reaction mixture was added into 200 ml of a cooled saturated solution of sodium hydrogencarbonate and the mixture was stirred at 0° C. for 30 minutes. The mixture was extracted with 1500 ml of ether, and the ether layer was washed with water, shaken with a saturated aqueous solution of copper sulfate, washed with water, shaken with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation, and the residue was subjected to the silica gel column chromatography (300 g of 230-400 mesh silica gel, n-hexane/ethyl acetate=4/1, 0.3 kg/cm2). Fractions of 100 ml were collected and the 35th to 37th fractions were combined to obtain 12.58 g (yield=84.0%) of 2'-acetoxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone in the form of a yellow oil.

Workup

  1. customa reaction
  2. stirringthe mixture was stirred at 0° C. for 30 minutes
  3. extractionThe mixture was extracted with 1500 ml of ether
  4. washthe ether layer was washed with water
  5. stirringshaken with a saturated aqueous solution of copper sulfate
  6. washwashed with water
  7. stirringshaken with a saturated aqueous solution of sodium chloride
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solvent was removed from the filtrate by distillation
  11. customFractions of 100 ml were collected

Sources & evidence

ORD record
ord-6f3806cb16914858b4b7abc304b3aacd
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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