Ammonium Chloride → HCID 57460956, compound

HRID 1674303Notes

Reaction equation

HRID 1674303 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][C:7]([CH3:11])([CH3:10])[CH:8]=[O:9])=[CH:4][CH:3]=1.[CH3:14][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][C:7]([CH3:10])([CH3:11])[CH:8]([OH:9])[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15192046HCID 15192046, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57460956HCID 57460956, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-bromophenoxy)-2-methylpropanal (5.3 g) in tetrahydrofuran (100 mL) was added methylmagnesium bromide (9.5 mL, 3 M diethyl ether solution) at −20° C., and the mixture was stirred for 1 hr. A saturated ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (4.0 g, 70%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with 1 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-67a5fffd61294ef79446a65693952436
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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