2-Amino-5-iodobenzenemethanol → 2-Amino-5-iodobenzaldehyde

HRID 986019Notes

Reaction equation

HRID 986019 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH2:4][OH:5]>ClCCl.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 1

HCID 142210292-Amino-5-iodobenzenemethanol

Product 1

HCID 142210302-Amino-5-iodobenzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (0.044 g) was added to a stirred solution of 2-amino-5-iodobenzyl alcohol (0.125 g) in dichloromethane (10 cm3) and the mixture was stirred for 6 hours. A further portion of manganese dioxide (0.044 g) was then added and stirring was continued for 16 hours. The mixture was then filtered, the filtrate evaporated in vacuo, and the residue chromatographed on silica (Merck "MK 60.9385") eluting with ethyl acetate. The requisite fractions were combined and concentrated in vacuo to afford 2-amino-5-iodobenzaldehyde. 0.5H2O as a solid, m.p. 105°, (0.1 g).

Workup

  1. stirringstirring
  2. waitwas continued for 16 hours
  3. filtrationThe mixture was then filtered
  4. customthe filtrate evaporated in vacuo
  5. customthe residue chromatographed on silica (Merck "MK 60.9385")
  6. washeluting with ethyl acetate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb39ad95ac6343308c071981dc3a9c81
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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