1-Dodecanethiol → 1-(n-Dodecylthio)-3-isopropoxy-2-propanol

HRID 259267

Reaction equation

HRID 259267 reaction equation
[CH:1]([O:4][CH2:5][CH:6]1[O:8][CH2:7]1)([CH3:3])[CH3:2].[H-].[Na+].[CH3:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][SH:23]>O1CCCC1>[CH2:22]([S:23][CH2:7][CH:6]([OH:8])[CH2:5][O:4][CH:1]([CH3:2])[CH3:3])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

5

Reactant 3

HCID 81951-DodecanethiolHCID 199202-((1-Methylethoxy)methyl)oxiraneHCID 24758Sodium hydride

Product 1

HCID 214239641-(n-Dodecylthio)-3-isopropoxy-2-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

2,3-Epoxypropyl isopropyl ether (1.16 g.) in several ml. of dry tetrahydrofuran is added to a stirred suspension formed by the addition of 50 mg. of sodium hydride (56% dispersion in mineral oil) to 2.2 g. 8. of n-dodecylthiol in 50 ml. tetrahydrofuran. The mixture is then stirred at 60° C. After approximately 4 hours the solvent is removed from the reaction mixture and 20 ml. of water is added to the residue. The resultant aqueous mixture is extracted with ether and the ether extracts washed with water, dried over magnesium sulfate and evaporated to yield 1-(n-dodecylthio)-3-isopropoxy-2-propanol.

Workup

  1. customformed by the addition of 50 mg
  2. customAfter approximately 4 hours the solvent is removed from the reaction mixture and 20 ml
  3. additionof water is added to the residue
  4. extractionThe resultant aqueous mixture is extracted with ether
  5. washthe ether extracts washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-1f4109b6444941dcb8d0392730d445b1
Source dataset
uspto-grants-1977_07
Patent number
US04036974

Linked notes

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