Lithium borohydride → 2-(Hydroxymethyl)-5-iodophenol

HRID 1585875Notes

Reaction equation

HRID 1585875 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:5]=1[OH:11].[Li+].[BH4-]>C1COCC1>[OH:11][C:5]1[CH:6]=[C:7]([I:10])[CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 11380407Methyl 4-iodosalicylate

Product 1

HCID 187797342-(Hydroxymethyl)-5-iodophenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl-2-hydroxy-4-iodo-benzoate from Step 2 (17.8 g, 64 mmol) was dissolved in THF. LiBH4 (3.07 g, 144 mmol) was added portionwise. The reaction mixture was heated at 50° for 16 hours. The reaction mixture was quenched carefully with 1N HCl and then extracted with EtOAc (3×). The organic layers were combined, washed with brine, dried (MgSO4) filtered and concentrated to yield the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was heated at 50° for 16 hours
  2. customThe reaction mixture was quenched carefully with 1N HCl
  3. extractionextracted with EtOAc (3×)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-52116cfd86614e5ebc9799a2f4f91065
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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