2-Chloroethanol → HCID 21487243, compound

HRID 1974366Notes

Reaction equation

HRID 1974366 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:18](O)[CH2:19][Cl:20].O>C1(C)C=CC=CC=1.C(OC(C)C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:20][CH2:19][CH2:18][O:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 342-ChloroethanolHCID 962WaterHCID 866702,3-Dihydro-3-hydroxy-2-phenyl-1H-isoindol-1-one

Product 1

HCID 21487243HCID 21487243, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

3-(2-Chloroethoxy)-2-phenyl-isoindolin-1-one can be obtained by refluxing a solution of 3-hydroxy-2-phenyl-isoindolin-1-one (22.5 g.) and glycol monochlorohydrin (7.7 g.) in anhydrous toluene (200 cc.) in the presence of p-toluenesulphonic acid (0.5 g.) in a Dean-Stark apparatus. Heating is continued until all the water formed has been entrained azeotropically. The cooled reaction mixture is then washed with 2N sodium hydroxide solution (50 cc.) and then with water (2 × 50 cc.). The organic solution obtained is dried over sodium sulphate and concentrated to dryness under reduced pressure. The residue obtained is taken up in diisopropyl ether (50 cc.) and the insoluble product is filtered off and washed with diisopropyl ether (6 cc.). After drying, 3-(2-chloroethoxy)-2-phenyl-isoindolin-1-one (20.1 g.), which melts at 71° C., is obtained.

Workup

  1. temperatureHeating
  2. customformed
  3. customThe cooled reaction mixture
  4. washis then washed with 2N sodium hydroxide solution (50 cc.)
  5. customThe organic solution obtained
  6. dry with materialis dried over sodium sulphate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue obtained
  9. filtrationthe insoluble product is filtered off
  10. washwashed with diisopropyl ether (6 cc.)
  11. customAfter drying

Sources & evidence

ORD record
ord-d3f105e14c0747f49b24101a2382ba05
Source dataset
uspto-grants-1976_12
Patent number
US04000306

Reaction notes

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