Sodium Chloride → 2-(2-Methoxyphenyl)acetaldehyde

HRID 408492

Reaction equation

HRID 408492 reaction equation
S(=O)(=O)=O.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][OH:15].C(N(CC)CC)C.[Cl-].[Na+]>CS(C)=O.ClCCl>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH:14]=[O:15]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 24682Sulfur trioxideHCID 819092-Methoxyphenethyl alcohol

Product 1

HCID 2695482-(2-Methoxyphenyl)acetaldehydeYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of pyridine complex with sulfur trioxide (134 g, 0.842 mol) in dimethylsulfoxide (150 mL) was slowly added to a solution of 2-(2-methoxy-phenyl)-ethanol (43 g, 0.28 mol) and triethylamine (86 g, 0.85 mol) in dichloromethane (500 mL) at 0° C. After being stirred 30 min, the mixture was poured into a saturated aqueous solution of sodium chloride and the organic layer was washed with dilute hydrochloric acid, a saturated aqueous solution of sodium chloride, dried over sodium sulfate and evaporated to dryness to give (2-methoxy-phenyl)-acetaldehyde (36 g, 0.24 mol, 86%) which was used in the next step directly.

Workup

  1. washthe organic layer was washed with dilute hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-74a84c87c09243949b11f5548591bc27
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Linked notes

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