Water → Methyl 3-hydroxy-4-iodobenzoate

HRID 1602689Notes

Reaction equation

HRID 1602689 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].S(=O)(=O)(O)O.O.[C:18](=O)(O)[O-].[Na+]>CO>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:18])=[O:7])=[CH:4][C:3]=1[OH:11]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 7368543-Hydroxy-4-iodobenzoic acid

Product 1

HCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-iodo-3-hydroxybenzoic acid (2.71 g, 10 mmol) and sulphuric acid (0.7 ml) in methanol (17 ml) is refluxed for 6 h. 20 ml of water are added and the mixture is basified with sodium bicarbonate until neutral. The mixture is extracted with ethyl ether (60 ml). The organic phase is washed with twice 30 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 a column of silica (50% ethyl acetate, 50% heptane).

Workup

  1. extractionThe mixture is extracted with ethyl ether (60 ml)
  2. washThe organic phase is washed with twice 30 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 a column of silica (50% ethyl acetate, 50% heptane)

Sources & evidence

ORD record
ord-eed7ea2a57464674abe866e58b150719
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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