Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 2-(2-Chloroethoxy)benzaldehyde

HRID 1789363Notes

Reaction equation

HRID 1789363 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:10][CH2:11][CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:10][CH2:11][CH2:12][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

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

Product 1

HCID 38414102-(2-Chloroethoxy)benzaldehydeYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40.0 g of 2-hydroxybenzaldehyde, 84 g of 1-chloro-2-tosyloxyethane and 50 g of potassium carbonate are added to 270 ml of dimethylformamide, and the mixture is stirred at room temperature for 3 days. After the reaction, half of the solvent is removed under reduced pressure. About 600 ml of water are added to the residue, and the mixture is extracted with ether. The extract is washed with 10% sodium hydroxide solution and water, dried and then concentrated under reduced pressure to remove solvent. The residue is distilled at 116°-118° C./0.2-0.3 mmHg to give 2-(2-chloroethyloxy)benzaldehyde (51.9 g, yield: 86%) as a colorless oil. The properties of this compound are the same as those disclosed in J.O.C., 18, 1380-1402 (1953).

Workup

  1. customAfter the reaction, half of the solvent
  2. customis removed under reduced pressure
  3. additionAbout 600 ml of water are added to the residue
  4. extractionthe mixture is extracted with ether
  5. washThe extract is washed with 10% sodium hydroxide solution and water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove solvent
  9. distillationThe residue is distilled at 116°-118° C./0.2-0.3 mmHg

Sources & evidence

ORD record
ord-0a61adb5089146bbaafb86e29a4c179b
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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