Triacetoxyperiodinane → 4-(Non-1-oyl)benzaldehyde

HRID 1454335Notes

Reaction equation

HRID 1454335 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C(Cl)Cl>[C:24]([C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[O:38])=[CH:35][CH:34]=1)(=[O:23])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 596917614-(1-Hydroxynon-1-yl)benzaldehyde

Product 1

HCID 596918254-(Non-1-oyl)benzaldehydeYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (0.268 g, 0.632 mmol) was added to a solution of 4-(1-hydroxynon-1-yl)benzaldehyde (0.125 g, 0.505 mmol) from Step A in CH2Cl2 (3.0 ml). After 1 h, the reaction was filtered and concentrated. Silica gel chromatography eluting with 19:1 v/v hexane/EtOAc gave 0.107 g (0.446 mmol, 88%) of the title compound: 1H NMR (500 MHz) δ 10.1 (s, 1H), 8.10 (d, J=8.2, 2H), 7.97 (d, J=8.2, 2H), 3.00 (t, J=7.3, 2H), 1.70-1.8 (m, 2H), 1.22-1.42 (m, 10H), 0.88 (t, J=7.0, 3H).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated
  3. washSilica gel chromatography eluting with 19:1 v/v hexane/EtOAc

Sources & evidence

ORD record
ord-31a4dfaa3a1947bbaa813e11aba2b1d5
Source dataset
uspto-grants-2009_01
Patent number
US07479504B2

Reaction notes

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