2-Iodobenzylic alcohol → 2-Iodobenzaldehyde

HRID 1280192Notes

Reaction equation

HRID 1280192 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]>C(Cl)Cl.CCOCC>[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 1

HCID 1076292-Iodobenzylic alcohol

Product 1

HCID 6434392-Iodobenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Commercially available 2-iodobenzyl alcohol (10.0 g, 42.7 mmol) was dissolved in 200 mL CH2Cl2. Upon completion, the reaction was diluted with 250 mL Et2O. The product was recovered as a brown liquid (10.3 g, 104%). TLC: Rf 0.57 (3:1 hexanes/EtOAc). IR (neat): 3061, 2853, 2745, 1696, 1580, 1561. 1H-NMR (400 MHz, CDCl3): δ 10.07 (s, 1H, C1-H), 7.95 (dd, 1H, J=7.9, 1.0, C4-H), 7.88 (dd, 1H, J=7.7, 1.8, C7-H), 7.47 (td, 1H, J=7.5 0.8, C6-H), 7.29 (td, 1H, J=7.6, 1.8, C5-H). 13C-NMR (100 MHz, CDCl3): δ 195.1, 140.2, 135.1, 134.7, 129.9, 128.4, 100.5. EI-MS m/z (rel int): 232 (M+, 100), 231 ([M−H]+, 40), 203 ([M−CHO]+, 15), 105 ([M−I]+, 3).

Workup

  1. customThe product was recovered as a brown liquid (10.3 g, 104%)

Sources & evidence

ORD record
ord-33786e56943d42bdae05f59f5f8c2782
Source dataset
uspto-grants-2002_09
Patent number
US06448443B1

Reaction notes

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