Hydrochloric Acid → HCID 10878678, compound

HRID 1160569Notes

Reaction equation

HRID 1160569 reaction equation
C[O:2][CH:3](OC)/[C:4](/[CH3:17])=[CH:5]/[CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.Cl.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][O:7][CH2:6]/[CH:5]=[C:4](\[CH3:17])/[CH:3]=[O:2])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 11737201HCID 11737201, compound

Product 1

HCID 10878678HCID 10878678, compoundYield 120.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-({[(2E)-4,4-dimethoxy-3-methylbut-2-en-1-yl]oxy}methyl)-4-methoxybenzene (1.52 g, 5.71 mmol) was dissolved in acetonitrile (16.0 ml), followed by addition of 1N hydrochloric acid (4.00 ml) and the reaction solution was stirred at room temperature for one hour. Subsequently, 2N hydrochloric acid (4.00 ml) to the reaction solution was added and it was further stirred for four hours. The reaction solution was poured into a saturated aqueous solution of sodium hydrogen carbonate, which was then extracted with diethyl ether. After the organic layer was washed with water and brine sequentially, it was dried over anhydrous magnesium sulfate. The drying agent was filtered off and the organic layer was concentrated under reduced pressure to obtain the title compound (1.52 g) as a colorless oil.

Workup

  1. stirringit was further stirred for four hours
  2. extractionwas then extracted with diethyl ether
  3. washAfter the organic layer was washed with water and brine sequentially
  4. dry with materialit was dried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4c757e3d62064261be79a1c3f7c7457b
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

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