Ammonia → HCID 58079340, compound

HRID 1027367Notes

Reaction equation

HRID 1027367 reaction equation
N.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1)[CH2:7][CH:8]1[O:12][CH2:11][CH2:10][O:9]1.[Li]>C(O)C>[CH3:2][O:3][C:4]1[CH2:15][C:14]([O:16][CH3:17])=[CH:13][CH:6]([CH2:7][CH:8]2[O:9][CH2:10][CH2:11][O:12]2)[CH:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 3028194LithiumHCID 247277715-(1,3-Dioxolan-2-ylmethyl)-1,3-dimethoxybenzene

Product 1

HCID 58079340HCID 58079340, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-33 °C

Procedure

Ammonia (pre-dried using sodium and iron (III) chloride) (approx 60 mL) is allowed to distil into a flask containing 2-(3,5-dimethoxybenzyl)-[1,3]-dioxolane (1.0 g, 4.46 mmol) in ethanol (3 mL), and lithium wire is added portionwise to the reaction mixture until the reaction mixture retains a blue colour for ten minutes. Ethanol (1 mL) is then added, and the mixture stirred for 20-25 minutes at −33° C. The ammonia is evaporated, and the resultant mixture is taken up into saturated aqueous ammonium chloride solution (20 ml), and extracted with ethyl acetate (3×25 ml). The organic extracts are washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo to give 2-(3,5-dimethoxy-cyclohexa-2,5-dienylmethyl)-[1,3]-dioxolane.

Workup

  1. customto distil into a flask
  2. additionis added portionwise to the reaction mixture until the reaction mixture
  3. customfor ten minutes
  4. customThe ammonia is evaporated
  5. extractionextracted with ethyl acetate (3×25 ml)
  6. washThe organic extracts are washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-19c5ea9d480f49619d7a63a902ed952a
Source dataset
uspto-grants-2014_05
Patent number
US08735322B2

Reaction notes

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