Ammonium Chloride → HCID 12644950, compound

HRID 2360518Notes

Reaction equation

HRID 2360518 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[CH:11]([Mg]Cl)([CH3:13])[CH3:12].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]([OH:8])[CH:11]([CH3:13])[CH3:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 312444-MethoxybenzaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 12644950HCID 12644950, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.5 ml 4-methoxy-benzaldehyde in 10 ml of toluene is added dropwise at 8° C. to 7.4 ml of a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran. Then the mixture is allowed to come up to ambient temperature and stirred for 1 hour. Then the reaction is stopped by the addition of semisaturated aqueous ammonium chloride solution. The phases are separated and the aqueous phase is extracted with toluene. The combined organic phases are washed with semisaturated aqueous ammonium chloride solution and dried on magnesium sulphate. The solvents are eliminated in vacuo and the product thus obtained is further reacted directly.

Workup

  1. customto come up to ambient temperature
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with toluene
  4. washThe combined organic phases are washed with semisaturated aqueous ammonium chloride solution
  5. customdried on magnesium sulphate
  6. customthe product thus obtained
  7. customis further reacted directly

Sources & evidence

ORD record
ord-f7251c0cad2d4a1da32b9cd96532a368
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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