2-Mercaptoethanol → HCID 21317600, compound

HRID 1833452Notes

Reaction equation

HRID 1833452 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-06ec29cfc1c24cc2bb836b5953abdb47
Source dataset
uspto-grants-1978_01
Patent number
US04066675

Reaction notes

Loading…