2-Mercaptoethanol → HCID 21317600, compound

HRID 328769Notes

Reaction equation

HRID 328769 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[Na].Br[CH:7]([CH2:19][CH2:20][CH2:21][CH:22]([O:28][C:29](=[O:31])[CH3:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>CO>[OH:4][CH2:3][CH2:2][S:1][CH:7]([CH2:19][CH2:20][CH2:21][CH:22]([O:28][C:29](=[O:31])[CH3:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 5360545SodiumHCID 21317595Ethyl 8-bromo-12-acetoxyheptadecanoate

Product 1

HCID 21317600HCID 21317600, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Mercaptoethanol (31.2 g., 0.4 mole) is dissolved in a solution of sodium (9.2 g., 0.4 mole) in methanol (300 ml.). Ethyl 8-bromo-12-acetoxy-heptadecanoate (Example 1, Step E) (43.5 g., 0.1 mole) is added and the resulting solution is heated at reflux for 5 hours. Most of the methanol is then removed by evaporation in vacuo. Water (350 ml.) is added to the residue and the oily product taken up in ether, washed with water and brine and dried over sodium sulfate. Evaporation of the ether leaves the title compound as a yellow residual oil which is used in the next step without further purification.

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureat reflux for 5 hours
  3. customMost of the methanol is then removed by evaporation in vacuo
  4. additionWater (350 ml.) is added to the residue
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the ether

Sources & evidence

ORD record
ord-17e9edbdcf264740b0293c5731a02758
Source dataset
uspto-grants-1977_04
Patent number
US04018802

Reaction notes

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