4-Methoxyphenethyl alcohol → 4-Methoxyphenylacetaldehyde

HRID 1713637Notes

Reaction equation

HRID 1713637 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH2:30][OH:31])=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][CH:30]=[O:31])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 697054-Methoxyphenethyl alcoholHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate

Product 1

HCID 797824-Methoxyphenylacetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (3.2 g, 7.29 mmol, 1.1 equiv) is added in one portion to a mixture of 4-methoxyphenethyl alcohol (1.0 g, 6.63 mmol) and NaHCO3 (1.1 g, 13.2 mmol, 2.0 equiv) in CH2Cl2, under an argon atmosphere. The resulting mixture is stirred for 1 h at RT and directly loaded on a silica gel (60 g) column. Flash chromatography purification (CH2Cl2/Et2O, 95/5), affords the title compound as a colorless oil: ES-MS: 148.9 [M−H]−; single peak at tR=6.12 min (System 1); Rf=0.74 (CH2Cl2/Et2O, 95/5).

Workup

  1. customFlash chromatography purification (CH2Cl2/Et2O, 95/5)

Sources & evidence

ORD record
ord-b5fdf986340c4209a25a6124c646aa2d
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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