Phenolphthalein → HCID 53988615, compound

HRID 2291974Notes

Reaction equation

HRID 2291974 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].C1C=CC2C(C3C=CC(O)=CC=3)(C3C=CC(O)=CC=3)OC(=O)C=2C=1.C([O-])([O-])=O.[K+].[K+].[CH2:35]([O:37][C:38](=[S:48])[CH2:39][CH2:40][CH2:41][CH2:42][CH:43](Br)[CH2:44][CH2:45][CH3:46])[CH3:36]>O>[CH2:35]([O:37][C:38](=[S:48])[CH2:39][CH2:40][CH2:41][CH2:42][CH:43]([S:3][C:1](=[O:4])[CH3:2])[CH2:44][CH2:45][CH3:46])[CH3:36]

Participants

6

Reactant 4

HCID 4764PhenolphthaleinHCID 11430Potassium CarbonateHCID 544334916-Bromo-8-methylthiooctanoic acid ethyl esterHCID 178418634HCID 178418634, compound

Product 1

HCID 53988615HCID 53988615, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.6 grams (0.113 mole) of thioacetic acid in 20 ml of water-free ethanol were neutralized to phenolphthalein with 81 ml of 10% ethanolic potash solution (0.113 mole potassium hydroxide) and 29.7 grams (0.1 mole) of 6-bromo-8-methylthiooctanoic acid ethyl ether added. The mixture was heated at reflux for 6 hours in a nitrogen atmosphere and allowed to stand for 10 hours at room temperature. The precipitated potassium bromide was filtered off, the filtrate concentrated in a vacuum, the residue taken up in 300 ml of diethyl ether and filtered, the filtrate was washed twice, each time with 100 ml of water, dried with sodium sulfate and concentrated in a vacuum. There were obtained 26 grams (89% of theory) of crude 6-acetylthio-8-methylthiooctanoic acid ethyl ester.

Workup

  1. additionadded
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 6 hours in a nitrogen atmosphere
  4. filtrationThe precipitated potassium bromide was filtered off
  5. concentrationthe filtrate concentrated in a vacuum
  6. filtrationfiltered
  7. washthe filtrate was washed twice
  8. dry with materialeach time with 100 ml of water, dried with sodium sulfate
  9. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-7f2577e9e9ec44dcad70cc4d22fc3654
Source dataset
uspto-grants-1989_01
Patent number
US04800044

Reaction notes

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