Water → 2-(Hydroxymethyl)-4-iodophenol

HRID 2399306Notes

Reaction equation

HRID 2399306 reaction equation
[I:1][C:2]1[CH:10]=[C:6]([C:7](O)=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.B.O1CCCC1.O.C(OCC)(=O)C>O1CCCC1>[OH:11][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:10][C:6]=1[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 83885-Iodosalicylic acidHCID 8857Ethyl AcetateHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 125452592-(Hydroxymethyl)-4-iodophenolYield 84.21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-iodosalicylic acid (1 g, 0.378 mol) in anhydrous tetrahydrofuran (4 ml) at 0° C. was added dropwise borane-tetrahydrofuran complex (1.0M solution in tetrahydrofuran, 11.4 ml). After fifteen minutes at room temperature, the mixture was heated at reflux for two hours. Water and ethyl acetate were added to the cooled solution, the organic phase separated and evaporated to give crude product. The residue was washed with pentane to afford 0.8 g (84.21%) of 2-hydroxy-5-iodo-benzyl alcohol, m.p. 125° C.

Workup

  1. waitAfter fifteen minutes at room temperature
  2. temperaturethe mixture was heated
  3. temperatureat reflux for two hours
  4. customthe organic phase separated
  5. customevaporated
  6. customto give crude product
  7. washThe residue was washed with pentane

Sources & evidence

ORD record
ord-f0e0a0d2a2854f85a51128b9e04ba562
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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