Ammonium Chloride → 1-[4-[(2-Hydroxyphenyl)methyl]phenyl]ethanone

HRID 2219462Notes

Reaction equation

HRID 2219462 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][C:5]1[CH:16]=[CH:15][C:8]([C:9](N(OC)C)=[O:10])=[CH:7][CH:6]=1.[CH3:21][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[C:9]([C:8]1[CH:7]=[CH:6][C:5]([CH2:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[OH:1])=[CH:16][CH:15]=1)(=[O:10])[CH3:21]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23072812HCID 23072812, compoundHCID 178418573HCID 178418573, compound3×

Product 1

HCID 230727851-[4-[(2-Hydroxyphenyl)methyl]phenyl]ethanoneYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Next, 4-(2-hydroxybenzyl)-N-methoxy-N-methylbenzamide (250 mg, 0.921 mmol) was dissolved in tetrahydrofuran (10 mL), followed by addition of methylmagnesium bromide (12% in THF, 2.8 mL) at −20° C. After 15 minutes, a second addition of methylmagnesium bromide (12% in THF, 2.5 mL) was made, followed by a third addition of methylmagnesium bromide (12% in THF, 2.0 mL). After 10 minutes, saturated aqueous ammonium chloride was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was concentrated, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the titled compound (110 mg, 53%) as a colorless powder.

Workup

  1. waitAfter 10 minutes
  2. extractionwas then extracted twice with ethyl acetate
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter the solvent was concentrated
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-9eed6357b7d8413bb2f784d1037538d4
Source dataset
uspto-grants-2008_08
Patent number
US07414072B2

Reaction notes

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