3-Iodobenzyl alcohol → 3-Iodobenzaldehyde

HRID 1280193Notes

Reaction equation

HRID 1280193 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6]>C(Cl)Cl.CCOCC>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 1

HCID 423003-Iodobenzyl alcohol

Product 1

HCID 2526103-Iodobenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Commercially available 3-iodobenzyl alcohol (5.32 mL, 41.9 mmol) was dissolved in 200 mL CH2Cl2. Upon completion, the reaction was diluted with 250 mL Et2O. The product was recovered as off-white crystals (8.1 g, 83.4%) mp: 48.0-55.0° C. TLC: Rf 0.54 (3:1 hexanes/EtOAc). IR (neat): 3058, 2824, 2728, 1698, 1586, 1566. 1H-NMR (400 MHz, CDCl3): δ 9.93 (s, 1H, C1-H), 8.22 (t, 1H, J=1.6, C3-H), 7.96 (dt, 1H, J=7.7, 1.4, C5-H), 7.85 (dt, 1H, J=7.7, 1.3, C7-H), 7.29 (t, 1H, J=7.7, C6-H). 13C-NMR (125 MHz, CDCl3): δ 190.6, 143.1, 138.4, 138.0, 130.7, 128.8, 94.6. EI-MS m/z (rel int): 232 (M+, 100), 231 ([M−H]+, 25), 203 ([M−CHO]+, 14), 104 ([M−HI]+, 38).

Workup

  1. customThe product was recovered as off-white crystals (8.1 g, 83.4%) mp: 48.0-55.0° C

Sources & evidence

ORD record
ord-32af000e31094af98e0ecb2141048416
Source dataset
uspto-grants-2002_09
Patent number
US06448443B1

Reaction notes

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