1-Dodecanethiol → 1,2-Propanediol, 3-(dodecylthio)-

HRID 1439153Notes

Reaction equation

HRID 1439153 reaction equation
[CH2:1]([SH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:14]1[O:16][CH:15]1[CH2:17][OH:18]>O.[OH-].[Li+]>[CH2:1]([S:13][CH2:14][CH:15]([OH:16])[CH2:17][OH:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 81951-DodecanethiolHCID 11164Glycidol

Product 1

HCID 866481,2-Propanediol, 3-(dodecylthio)-

Reagents, catalysts & solvents 1

HCID 168937Lithium hydroxide, monohydrateCatalyst

Procedure

To a 300-ml flask was added 60.7 grams (0.30 mole) of n-dodecyl mercaptan and 0.63 grams (0.015 mole, 5 mole percent) of lithium hydroxide monohydrate catalyst. The mixture was stirred and heated to 90°-100° C. To this stirred solution was added dropwise over a 4.25 hour period 33.3 grams (0.45 mole) of glycidol. The reaction mixture was stirred and heated at 90°-95° C for an additional 21 hours. The product was isolated by vacuum distillation in a yield of 41.3 grams (50% of theory) boiling at 158°-178° C/0.05-0.15 mm.

Workup

  1. temperatureheated to 90°-100° C
  2. stirringThe reaction mixture was stirred
  3. temperatureheated at 90°-95° C for an additional 21 hours
  4. customThe product was isolated by vacuum distillation in a yield of 41.3 grams (50% of theory) boiling at 158°-178° C/0.05-0.15 mm

Sources & evidence

ORD record
ord-fabb8adeecf943d2b324954e5d898330
Source dataset
uspto-grants-1977_11
Patent number
US04058502

Reaction notes

Loading…