Ammonium Chloride → HCID 57678401, compound

HRID 491505Notes

Reaction equation

HRID 491505 reaction equation
[CH3:1][Mg]Br.[NH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13](=[O:15])[CH3:14])=[C:7]([O:16][CH3:17])[CH:6]=1.[Cl-].[NH4+]>O1CCCC1.O>[NH2:4][C:5]1[CH:6]=[C:7]([O:16][CH3:17])[C:8]([C:13]([OH:15])([CH3:1])[CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 576784271-(4-Amino-2,6-dimethoxyphenyl)ethan-1-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 57678401HCID 57678401, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl magnesium bromide (3M in ether, 16.8 mL, 50.5 mmol) in anhydrous tetrahydrofuran (20 mL), cooled in an ice bath, was added 1-(4-amino-2,6-dimethoxy-phenyl)-ethanone (2.19 g, 11.2 mmol-dissolved in 65 mL anhydrous tetrahydrofuran), maintaining the reaction temperature below 10° C. After stirring 4 hours at room temperature, 10% ammonium chloride (20 mL) was added, maintaining the temperature of the reaction below 20° C. (with the use of an ice bath) during the addition. The mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried using anhydrous sodium sulfate, filtered and concentrated to yield 2-(4-Amino-2,6-dimethoxy-phenyl)-propan-2-ol (2.23 g, 94%) as a pale yellow solid.

Workup

  1. temperaturemaintaining the reaction temperature below 10° C
  2. temperaturemaintaining
  3. customthe temperature of the reaction below 20° C. (with the use of an ice bath)
  4. additionduring the addition
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-205d495c5d7b407485d811e2893cfb4e
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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