Sodium Hydroxide → HCID 54550855, compound

HRID 848553Notes

Reaction equation

HRID 848553 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[CH:10]([CH2:21][CH2:22][S:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]([O:13]CC1C=CC=CC=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[CH2:1]([O:8][C:9](=[O:30])[CH:10]([CH2:21][CH2:22][S:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54236851HCID 54236851, compound

Product 1

HCID 54550855HCID 54550855, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

21.2 g of 2-(2-phenylthioethyl)malonic acid dibenzyl ester are dissolved in 70 ml of dioxan. The solution is heated to 70°, and, whilst stirring, 50.5 ml of 1 N sodium hydroxide solution are added. Stirring is continued for 20 minutes at 70°, the mixture is cooled and the dioxan is distilled off at 40° under reduced pressure. The aqueous solution is covered with a layer of 100 ml of ether and acidified at 0° with 35 ml of 2 N hydrochloric acid. The ether phase is separated off and the aqueous phase extracted twice with 100 ml of ether each time. The combined ether phases are extracted with 100 ml of 0.5 N potassium bicarbonate solution and then three times with 50 ml of 2 N sodium carbonate solution each time. The combined sodium carbonate solutions are acidified at 0° with 2 N hydrochloric acid. The oil that precipitates is dissolved by extracting three times with 60 ml of chloroform each time. The combined chloroform solutions are dried over magnesium sulphate and concentrated by evaporation under reduced pressure. The residue is dried for 15 hours at room temperature at 0.1 torr. 2-(2-Phenylthioethyl)malonic acid monobenzyl ester is obtained as a colourless oil.

Workup

  1. temperatureThe solution is heated to 70°
  2. stirringStirring
  3. temperaturethe mixture is cooled
  4. distillationthe dioxan is distilled off at 40° under reduced pressure
  5. customacidified at 0° with 35 ml of 2 N hydrochloric acid
  6. customThe ether phase is separated off
  7. extractionthe aqueous phase extracted twice with 100 ml of ether each time
  8. extractionThe combined ether phases are extracted with 100 ml of 0.5 N potassium bicarbonate solution
  9. customare acidified at 0° with 2 N hydrochloric acid
  10. customThe oil that precipitates
  11. dissolutionis dissolved
  12. extractionby extracting three times with 60 ml of chloroform each time
  13. dry with materialThe combined chloroform solutions are dried over magnesium sulphate
  14. concentrationconcentrated by evaporation under reduced pressure
  15. customThe residue is dried for 15 hours at room temperature at 0.1 torr

Sources & evidence

ORD record
ord-0371f1298a2049f68d233c0b71e89771
Source dataset
uspto-grants-1981_10
Patent number
US04296128

Reaction notes

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