Water → 2-(2-Chloroethoxy)benzaldehyde

HRID 85121

Reaction equation

HRID 85121 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][Cl:14])(=O)=O)=CC=1.[OH:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[O:19].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:14][CH2:13][CH2:12][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 6998SalicylaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 38414102-(2-Chloroethoxy)benzaldehydeYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2-chloroethyl 4-methylbenzenesulfonate (39; 27.0 g, 0.115 mol), 2-hydroxybenzaldehyde (25; 14.0 g, 0.115 mol) and K2CO3 (31.7 g, 0.23 mol) in DMF (100 mL) was stirred at 45° C. for 12 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (3×150 mL). The combined organic layers were washed saturated brine (3×50 mL), dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1) to give 2-(2-chloroethoxy)benzaldehyde 40 (16.8 g, 0.091 mol, 79%) as a pale yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×150 mL)
  2. washThe combined organic layers were washed saturated brine (3×50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-6da4d1c38e6b48daa484e9aa72be25fb
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Linked notes

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