Water → Methyl 4-hydroxy-3-iodobenzoate

HRID 1602695Notes

Reaction equation

HRID 1602695 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.O.[C:18](=O)(O)[O-].[Na+]>CO>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH3:18])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 4494734-Hydroxy-3-iodobenzoic acid (2IPCOOH)HCID 516892Sodium Bicarbonate

Product 1

HCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-iodo-4-hydroxybenzoic acid (28.76 g, 0.11 mol) and sulphuric acid (6.6 ml) in methanol (160 ml) is refluxed for 6 h. 300 ml of water are added and the mixture is basified with sodium bicarbonate until neutral. It is extracted with ethyl ether (600 ml). The organic phase is washed with twice 400 ml of water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is purified by flash chromatography on the column of silica (10% ethyl acetate, 90% CH2Cl2).

Workup

  1. extractionIt is extracted with ethyl ether (600 ml)
  2. washThe organic phase is washed with twice 400 ml of water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  5. customThe product is purified by flash chromatography on the column of silica (10% ethyl acetate, 90% CH2Cl2)

Sources & evidence

ORD record
ord-ab20258afc15411dbd3ce7443a81de6a
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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