Triethylamine → HCID 21705008, compound

HRID 1595526Notes

Reaction equation

HRID 1595526 reaction equation
[CH3:1][CH:2]([S:4](Cl)(=[O:6])=[O:5])[CH3:3].[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[CH3:1][CH:2]([S:4]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([CH:22]=[O:23])=[CH:24][CH:25]=2)=[CH:11][CH:10]=1)(=[O:6])=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 824082-Propanesulfonyl chlorideHCID 217050114-[2-(4-Hydroxyphenyl)ethoxy]benzaldehyde

Product 1

HCID 21705008HCID 21705008, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.77 g (13 mmole) 2-propanesulfonyl chloride dissolved in dichloromethane was slowly added to a solution of 3.2 g (13 mmole) 4-[2-(4-hydroxyphenyl)ethoxy]benzaldehyde and 2.63 g (26 mmole) triethylamine in 80 ml dichloromethane at 0° C. The temperature was slowly allowed to rise to room temperature and when the starting material was consumed the reaction mixture was poured on to ice. The phases were separated and the organic phase was washed with sodium carbonate, dried (sodium sulfate), filtered and evaporated. The residue was purified by chromatography on silica gel using dichloromethane as eluent to give 3.3 g (yield 72.8%) of 4-[2-(4-formylphenoxy)ethyl]phenyl 2-propanesulfonate.

Workup

  1. customto rise to room temperature
  2. customwhen the starting material was consumed the reaction mixture
  3. additionwas poured on to ice
  4. customThe phases were separated
  5. washthe organic phase was washed with sodium carbonate
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7bfdd98331f14d39b13d7ad0239adcd4
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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