Sulfuric Acid → Methyl 4-hydroxy-3-iodobenzoate

HRID 523507

Reaktionsgleichung

Reaktionsgleichung von HRID 523507
[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.Cl[CH2:18]Cl.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[OH:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([O:7][CH3:18])=[O:6])=[CH:3][C:2]=1[I:1]

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 6344Dichloromethane2×HCID 4494734-Hydroxy-3-iodobenzoic acid (2IPCOOH)HCID 516892Sodium Bicarbonate

Produkt 1

HCID 11346465Methyl 4-hydroxy-3-iodobenzoateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-iodo-4-Hydroxybenzoic acid (7.25 g, 27.4 mmol) and sulfuric acid (1.9 ml, 36 mmol) in methanol is stirred at 55° C. for 6 hours. TLC (dichloromethane): 30% of starting material. The solution is stirred 12 h at room temperature. TLC (dichloromethane): 10% of starting material and stirred at 55° C. for 2 h. After cooling, ethyl acetate (200 mL) was added and the mixture was adjusted to pH 3 using sodium bicarbonate. The organic layer was washed two times with water and then dried over MgSO4. Filtration and rotary evaporation at 40° C. afforded a white solid. The solid was triturated with hexane, filtered off and dried under reduced pressure. M=4.47 g. Yield: 59%.

Aufarbeitung

  1. temperatureAfter cooling
  2. washThe organic layer was washed two times with water
  3. dry with materialdried over MgSO4
  4. filtrationFiltration and rotary evaporation at 40° C.
  5. customafforded a white solid
  6. customThe solid was triturated with hexane
  7. filtrationfiltered off
  8. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1e968f892039401aba9e490a93f6d1d0
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09339486B2

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