Ammonia → HCID 15557865, compound

HRID 1606314Notes

Reaction equation

HRID 1606314 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.N.[Na].[Cl-].[NH4+]>C(O)C>[OH:8][CH2:7][C:6]1[CH2:5][CH:4]=[C:3]([O:2][CH3:1])[CH2:10][CH:9]=1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 77384-Methoxybenzyl alcoholHCID 25517Ammonium ChlorideHCID 5360545Sodium2×

Product 1

HCID 15557865HCID 15557865, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using the method of Birch, J. Proc. Roy. Soc. New South Wales, 83, 245 (1949), 27.6 g of 4-methoxybenzyl alcohol in 93 ml of dry ethanol was added to 600 ml of liquid ammonia and reduced with 23 g of sodium added in pieces. After 2 hrs stirring, the excess sodium was discharged by cautiously adding 60 g of ammonium chloride. The ammonia was allowed to evaporate, water was added to the residue, and the product was extracted with dichloromethane. The extracts, dried and evaporated, afforded 12.1 g, bp 72°-74° (0.1 mm), identified by nmr.

Workup

  1. additionadded in pieces
  2. customto evaporate
  3. additionwater was added to the residue
  4. extractionthe product was extracted with dichloromethane
  5. customThe extracts, dried
  6. customevaporated
  7. customafforded 12.1 g, bp 72°-74° (0.1 mm)

Sources & evidence

ORD record
ord-62697a478b054557987d3d21f43b10a7
Source dataset
uspto-grants-1976_04
Patent number
US03952114

Reaction notes

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