Diethyl Ether → 2-(4-Chlorophenyl)acetaldehyde

HRID 1614895Notes

Reaction equation

HRID 1614895 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 74647p-Chlorophenethylic alcoholHCID 159087Triacetoxyperiodinane

Product 1

HCID 114125022-(4-Chlorophenyl)acetaldehydeYield 42.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chlorophenyl)ethanol (2.00 g, 12.77 mmol) in dichloromethane (100 ml) was added Dess-Martin periodinane (8.12 g, 19.16 mmol) and the mixture was stirred at room temperature over weekend. Then was added diethylether (150 ml) and the resulting mixture was washed with a 1:1 solution (150 ml) of sodium carbonate (aqueous saturated) and sodium thiosulfate (aqueous saturated) and then with sodium bicarbonate (aqueous saturated) and finally with brine. The organic phase was then dried over sodium sulfate and evaporated. Silica gel flash chromatography (pentan/ethylacetate:9/1) afforded the desired compound (0.834 g, 42%) as a white solid.

Workup

  1. washthe resulting mixture was washed with a 1:1 solution (150 ml) of sodium carbonate (aqueous saturated) and sodium thiosulfate (aqueous saturated)
  2. dry with materialThe organic phase was then dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-37780e14cbc94731a44ff98695f6075f
Source dataset
uspto-grants-2014_07
Patent number
US08765728B2

Reaction notes

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