Water → 2-(Hydroxymethyl)-5-iodophenol

HRID 636769Notes

Reaction equation

HRID 636769 reaction equation
B.[OH:2][C:3]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].O>C1COCC1>[OH:2][C:3]1[CH:11]=[C:10]([I:12])[CH:9]=[CH:8][C:4]=1[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 728742-Hydroxy-4-iodobenzoic acid

Product 1

HCID 187797342-(Hydroxymethyl)-5-iodophenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1M solution of borane in THF was added dropwise at 0° C. to a solution of 2-hydroxy-4-iodobenzoic acid (13.2 g, 0.05 mol) in THF (100 ml). The mixture was stirred for 6 hours at room temperature and 20 ml of a solution of THF and water (1:1) were then added. After concentration on a rotary evaporator under vacuum at 40° C. The residue was extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator under vacuum at 40° C. The product was purified by flash chromatography on a column of silica (60% EtOAc, 40% heptane). Its properties were as follows:

Workup

  1. concentrationAfter concentration
  2. customon a rotary evaporator under vacuum at 40° C
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  7. customThe product was purified by flash chromatography on a column of silica (60% EtOAc, 40% heptane)

Sources & evidence

ORD record
ord-e987212be35044cea1a3ad50a5c8ed32
Source dataset
uspto-grants-2001_02
Patent number
US06194450B1

Reaction notes

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