p-Toluenesulfonic acid → HCID 21417759, compound

HRID 437615Notes

Reaction equation

HRID 437615 reaction equation
[SH:1][CH2:2][CH2:3][CH:4]([OH:6])[CH3:5].[C:7]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:8][C:9]([CH3:11])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:14]([O:13][C:7](=[O:12])[CH2:8][C:9]1([CH3:11])[S:1][CH2:2][CH2:3][CH:4]([CH3:5])[O:6]1)[CH3:15]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8868Ethyl AcetoacetateHCID 516892Sodium BicarbonateHCID 37034451-mercaptobutan-3-ol

Product 1

HCID 21417759HCID 21417759, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

75 ml of dichloromethane is placed into a 100 ml round-bottom flask. To the dichloromethane is added 5.3 grams (0.05 moles) of 4-mercapto-2-butanol. 7.14 grams (0.055 moles) ethyl acetoacetate is then added followed by 0.1 grams of p-toluene sulfonic acid. Boiling chips are added to the flask. A Dean-Starke distilling receiver is placed on the flask, and a reflux condenser is placed on the receiver. The flask is then heated slowly until reflux occurs, and then the temperature is increased for a more vigorous reflux. The reflux lasts for a period of 2 hours before water of reaction ceases to be formed. The reaction mass is then cooled and neutralized with 10% aqueous sodium bicarbonate to a pH of 8. The reaction mass is filtered through fluted filter paper, and the dichloromethane solvent is removed by means of rotary evaporation. 9.8 grams of crude product are recovered after the rotary evaporation operation. The crude product is then distilled by means of vacuum distillation yielding the following 4 fractions:

Workup

  1. additionBoiling chips are added to the flask
  2. distillationA Dean-Starke distilling receiver
  3. temperatureThe flask is then heated slowly
  4. temperatureuntil reflux
  5. temperaturethe temperature is increased for a more vigorous reflux
  6. customThe reflux lasts for a period of 2 hours before water of reaction ceases
  7. customto be formed
  8. temperatureThe reaction mass is then cooled
  9. filtrationThe reaction mass is filtered
  10. filtrationthrough fluted filter paper
  11. customthe dichloromethane solvent is removed by means of rotary evaporation
  12. custom9.8 grams of crude product are recovered after the rotary evaporation operation
  13. distillationThe crude product is then distilled by means of vacuum distillation
  14. customyielding the following 4 fractions

Sources & evidence

ORD record
ord-097bd3322740482b99ad62e94375dd6e
Source dataset
uspto-grants-1977_06
Patent number
US04031257

Reaction notes

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