2-Mercaptoethanol → 3-[(2-Hydroxyethyl)thio]-1,2-propanediol

HRID 976495Notes

Reaction equation

HRID 976495 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].CN(C)CC1C=CC=CC=1.[CH2:15]1[O:17][CH:16]1[CH2:18][OH:19]>CC(CC(C)=O)C>[OH:4][CH2:3][CH2:2][S:1][CH2:15][CH:16]([OH:17])[CH2:18][OH:19]

Participants

5

Conditions

Temperature
50 °C

Procedure

In a reaction vessel equipped with a stirrer, a cooling tube, a nitrogen introducing tube and a thermometer, 78.1 parts of 2-mercaptoethanol was charged, and 2-mercaptoethanol was diluted with 159.6 parts of MIBK. Then, 0.41 part of dimethylbenzylamine was added and, after heating to 50° C., 81.5 parts of glycidol was added dropwise with stirring over 3 hours in a dry nitrogen atmosphere. The reaction vessel was cooled and maintained at 50° C. 2 Hours after dropping, it was confirmed that an absorption of --SH (2540 cm-1) and an absorption of a glycidyl group (910 cm-1) are disappeared by the measurement of infrared spectra. Further, the reaction product had no mercapto-like odor. Thereafter, MIBK was removed under reduced pressure to give 1-(2-hydroxyethylthio)-2,3-propanediol as a viscous liquid. Yield was 90% of the charge weight.

Workup

  1. customIn a reaction vessel equipped with a stirrer, a cooling tube, a nitrogen introducing tube
  2. temperatureThe reaction vessel was cooled
  3. temperaturemaintained at 50° C
  4. customit was confirmed that an absorption of --SH (2540 cm-1)
  5. customan absorption of a glycidyl group (910 cm-1)
  6. customThereafter, MIBK was removed under reduced pressure

Sources & evidence

ORD record
ord-85c83228136148a383cf6cfee9edcbb3
Source dataset
uspto-grants-1997_03
Patent number
US05612395

Reaction notes

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