Ammonium Chloride → HCID 59526852, compound

HRID 384471Notes

Reaction equation

HRID 384471 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[O:12][CH2:13][C:14]([CH3:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[O:12][CH2:13][C:14]([CH3:20])([OH:15])[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 598160891-[3-(Phenylmethoxy)phenoxy]-2-propanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 59526852HCID 59526852, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-[3-(Benzyloxy)phenoxy]acetone (1.77 g) was dissolved in THF (20 mL), and, a solution of 0.97M methyl magnesium bromide in THF (9.0 mL) was added dropwise thereto with cooling in an ice bath under nitrogen flow. The reaction mixture was stirred at room temperature for 2.5 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a 1M aqueous sodium hydroxide solution and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-85/15) to obtain 1-[3-(benzyloxy)phenoxy]-2-methylpropan-2-ol (997 mg).

Workup

  1. temperaturewith cooling in an ice bath under nitrogen flow
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a 1M aqueous sodium hydroxide solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-85/15)

Sources & evidence

ORD record
ord-61726d529b6b4f1d9c808ecab0f8787e
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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