Thioglycerol → (+/-)-1-S-hexadecylthioglycerol

HRID 977278Notes

Reaction equation

HRID 977278 reaction equation
[SH:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[OH-].[K+].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(O)C>[CH2:25]([S:1][CH2:2][CH:3]([CH2:4][OH:5])[OH:6])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH3:10]

Participants

5

Reactant 3

HCID 7291ThioglycerolHCID 82131-BromohexadecaneHCID 14797Potassium Hydroxide

Product 1

HCID 13002863(+/-)-1-S-hexadecylthioglycerolYield 950.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 40.0 grams (0.037 mole) 3-mercapto-1,2-propanediol in 300 milliliters of 95% ethanol, 24.9 grams (0.44 mole) of KOH was added under an inert atmosphere of nitrogen. Then, a solution of 135.0 grams (0.44 mole) bromohexadecane in 100 milliliters of 95% ethanol was added dropwise over a one-hour period, and the reaction allowed to proceed at room temperature with vigorous stirring for 24 hours. The precipitate was filtered, taken up in one liter of boiling methanol and cooled to 0° Centigrade for twelve hours. The precipitate was filtered and allowed to air dry, producing 117 grams (95%) of product (mp 72°-74° Centigrade).

Workup

  1. customto proceed at room temperature
  2. filtrationThe precipitate was filtered
  3. temperaturecooled to 0° Centigrade for twelve hours
  4. filtrationThe precipitate was filtered
  5. customto air dry

Sources & evidence

ORD record
ord-2f81c92e4dc44e7cb7e04f2b12e41f15
Source dataset
uspto-grants-1997_03
Patent number
US05614548

Reaction notes

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