3-Hydroxybenzaldehyde → 3-(2-(1-Pyrrolidinyl)ethoxy)benzaldehyde

HRID 619166Notes

Reaction equation

HRID 619166 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[OH-].[K+].CS(C)=O.Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>C(OCC)(=O)C.O>[N:20]1([CH2:19][CH2:18][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 107752443-(2-(1-Pyrrolidinyl)ethoxy)benzaldehydeYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-hydroxybenzaldehyde (4.15 g, 33.98 mmol), KOH (4.93 g) and DMSO (50 ml) was added N-(2-chloroethyl)pyrrolidine hydrochloride (6.94 g). The reaction mixture was stirred at room temperature overnight, then was poured into water (750 ml) and ethyl acetate (350 ml) was added. The layers were separated, the aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water (2×1000 ml), dried over MgSO4, filtered and stripped to afford 7.12 g of 3-[2-(1-pyrrolidinyl)ethoxy]benzaldehyde.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with water (2×1000 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-be5253fa1c614660b4f6a176ccdef78f
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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