Water → (4-Benzyloxy-3,5-dimethoxy-phenyl)-acetaldehyde

HRID 2382562Notes

Reaction equation

HRID 2382562 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][CH2:18][OH:19])=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>ClCCl>[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][CH:18]=[O:19])=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 574368712-(4-Benzyloxy-3,5-dimethoxy-phenyl)-ethanol

Product 1

HCID 57436872(4-Benzyloxy-3,5-dimethoxy-phenyl)-acetaldehydeYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-benzyloxy-3,5-dimethoxy-phenyl)-ethanol (1.0 g, 3.3 mmol) in dichloromethane (25 mL) was added Dess-Martin reagent (1.54 g, 3.6 mmol) and water (59 μL). After completion of addition the reaction continued to stir for 6 hours. The resulting precipitate was filtered off and the filtrate was concentrated. The crude material was purified using silica gel chromatography (gradient from 1:2 ethyl acetate:hexane to 1:1 ethyl acetate:hexane) to obtain the desired compound as a yellow oil (547 mg, 55%).

Workup

  1. additionAfter completion of addition the reaction
  2. filtrationThe resulting precipitate was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe crude material was purified

Sources & evidence

ORD record
ord-921af9bb7bf9460a98ea75c8539bcb49
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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