Ammonium Chloride → HCID 86707864, compound

HRID 922451Notes

Reaction equation

HRID 922451 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[CH3:14][Mg]Br.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]([OH:7])[CH3:14])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 123984504-Chloro-3,5-dimethoxybenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 86707864HCID 86707864, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3,5-dimethoxybenzaldehyde (1.0 g) in tetrahydrofuran (20 mL) was added dropwise a 3M solution of methylmagnesium bromide in diethyl ether (1.83 mL) under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. Then, thereto was added aqueous ammonium chloride solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated saline, and then dried over magnesium sulfate and concentrated under reduced pressure to give a crude product of 1-(4-chloro-3,5-dimethoxyphenyl)ethanol [REx(22-2)] (1.23 g) as a colorless powder.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was sequentially washed with water and saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64b277bec2194ac5b1b207257fda6acb
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

Loading…