Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 5-(2-Chloroethoxy)-2,3-dihydro-1H-inden-1-one

HRID 64900

Reaction equation

HRID 64900 reaction equation
[O-]CC.[Na+].[Na].[OH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2.C1(C)C=CC(S(O[CH2:27][CH2:28][Cl:29])(=O)=O)=CC=1>C(O)C>[Cl:29][CH2:28][CH2:27][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 2331475-Hydroxy-1-indanoneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 202358795-(2-Chloroethoxy)-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent4×

Procedure

To a solution of sodium ethoxide in ethanol prepared from 5.68 g of sodium and 500 ml of absolute ethanol, 36.75 g of 5-hydroxy-1-indanone in 500 ml of slightly-heated ethanol are added in the course of 30 minutes. Then, 74.5 g of β-chloroethyl p-toluenesulphonate in 100 ml of ethanol are dropwise added, and the mixture is refluxed under stirring for 25 hours. Then the mixture is cooled, the insolubilized sodium p-toluenesulphonate 40 g, dry) is filtered off, and the ethanol is evaporated till dryness under vacuum. The residue (71.6 g) is treated with water (250 ml) and methylene chloride (250 ml); the aqueous phase is extracted two further times with methylene chloride, and the organic extracts are washed twice with 100 ml of 10% sodium hydroxide and with water till neutralization. The solvent is evaporated and the residue (54 g) is purified over silica-gel column; by eluting with methylene chloride:hexane (9:1) the excess β-chloro-ethyl p-toluenesulphonate is separated, and the desired product is isolated with methylene chloride; 26.6 g (51%) of a yellow solid are obtained. M.P. 79°-82° C. and analysis correct.

Workup

  1. additionare added in the course of 30 minutes
  2. temperaturethe mixture is refluxed
  3. temperatureThen the mixture is cooled
  4. dry with materialthe insolubilized sodium p-toluenesulphonate 40 g, dry)
  5. filtrationis filtered off
  6. customthe ethanol is evaporated till dryness under vacuum
  7. additionThe residue (71.6 g) is treated with water (250 ml) and methylene chloride (250 ml)
  8. extractionthe aqueous phase is extracted two further times with methylene chloride
  9. washthe organic extracts are washed twice with 100 ml of 10% sodium hydroxide and with water till neutralization
  10. customThe solvent is evaporated
  11. customthe residue (54 g) is purified over silica-gel column
  12. washby eluting with methylene chloride:hexane (9:1) the excess β-chloro-ethyl p-toluenesulphonate
  13. customis separated

Sources & evidence

ORD record
ord-a7d20e05022d4fe9b2c7d93da7588474
Source dataset
uspto-grants-1986_09
Patent number
US04610998

Linked notes

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