Ammonium Chloride → HCID 61101071, compound

HRID 593388Notes

Reaction equation

HRID 593388 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10]1([CH3:18])[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1.[Cl-].[NH4+]>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:5]([C:13]2[CH:14]=[CH:15][C:10]([CH3:18])=[CH:11][CH:12]=2)[OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2526103-IodobenzaldehydeHCID 178418370HCID 178418370, compound

Product 1

HCID 61101071HCID 61101071, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 3-iodobenzaldehyde (10 g) in tetrahydrofuran (50 mL) at 30° C. is added a 0.43M solution of p-tolylmagnesium bromide in tetrahydrofuran. After stirring at 50° C. for 1 hour, the reaction mixture is hydrolyzed with a saturated aqueous solution of ammonium chloride and extracted ethyl acetate. Pooled organic extracts are washed with brine, dried over magnesium sulfate and concentrated. The residue is purified by column chromatography over silica gel (gradient heptane/ethyl acetate 95/5 to 90/10) to yield (3-iodophenyl)-p-tolylmethanol.

Workup

  1. extractionextracted ethyl acetate
  2. washPooled organic extracts are washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography over silica gel (gradient heptane/ethyl acetate 95/5 to 90/10)

Sources & evidence

ORD record
ord-8374651bd8e746268f965a3292348331
Source dataset
uspto-grants-2016_01
Patent number
US09242959B2

Reaction notes

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