Water → 1-(3-Iodophenyl)ethan-1-ol

HRID 1364404Notes

Reaction equation

HRID 1364404 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[CH:5]=1)=[O:3].[BH4-].[Na+].O.[Cl-].[NH4+]>CO>[I:10][C:6]1[CH:5]=[C:4]([CH:2]([OH:3])[CH3:1])[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 84449Ethanone, 1-(3-iodophenyl)-HCID 4311764Sodium borohydride

Product 1

HCID 252659661-(3-Iodophenyl)ethan-1-olYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold (ice water) solution of 3-iodoacetophenone (2.59 gm; 10.5 mmol) in methanol (10 mL) is added sodium borohydride (395 mg; 10.4 mmol) is stirred for thirty minutes. Water (10 mL) is added to the solution and stirred 15 minutes. Saturated ammonium chloride (40 mL) is added and the solution is extracted with ethyl acetate. The organics are separated and dried over magnesium sulfate. The solvent is removed to give 2.26 grams of 1-(3-iodophenyl)-ethanol.

Workup

  1. stirringstirred 15 minutes
  2. extractionthe solution is extracted with ethyl acetate
  3. customThe organics are separated
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed

Sources & evidence

ORD record
ord-e5ace26b089e47659d184269be6faf2b
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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