Methanol → Methyl 3-(hydroxymethyl)-5-iodobenzoate

HRID 1740305Notes

Reaction equation

HRID 1740305 reaction equation
CO.[I:3][C:4]1[CH:5]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[CH:7]=[C:8]([CH:13]=1)[C:9](OC)=[O:10].[BH4-].[Na+].C(OCC)(=O)C>O1CCCC1.O>[OH:10][CH2:9][C:8]1[CH:13]=[C:4]([I:3])[CH:5]=[C:6]([CH:7]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 2758568Dimethyl 5-iodoisophthalateHCID 4311764Sodium borohydride

Product 1

HCID 21837989Methyl 3-(hydroxymethyl)-5-iodobenzoateYield 82.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methanol (20 ml) was added dropwise to a mixture of dimethyl 5-iodoisophthalate (20.0 g) and sodium borohydride (2.4 g) in tetrahydrofuran (200 ml) for 15 minutes at 45-50° C., and the mixture was stirred for 1 hour at same temperature. The reaction mixture was added to a mixture of ethyl acetate and water, and the separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform-methanol (19:1, V/V) as an eluent. The fractions containing the desired product were collected and evaporated in vacuo to give methyl 5-hydroxymethyl-3-iodobenzoate (15.11 g).

Workup

  1. washthe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel with chloroform-methanol (19:1, V/V) as an eluent
  5. additionThe fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-48bcaedafb75487f926df3a4fd7a867d
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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