Acetic Acid → HCID 86737538, compound

HRID 126743Notes

Reaction equation

HRID 126743 reaction equation
[O-][CH2:2][CH3:3].[Na+].C1([SH:11])C=CC=CC=1.Br[CH:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:29](O)(=O)[CH3:30].[CH2:33](O)[CH3:34]>>[C:3]1([CH:23]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:24]([O:26][CH2:27][CH3:28])=[S:11])[CH:2]=[CH:30][CH:29]=[CH:34][CH:33]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 702Ethanol3×HCID 7969ThiophenolHCID 2723922Sodium ethoxideHCID 13055673HCID 13055673, compound

Product 1

HCID 86737538HCID 86737538, compound

Procedure

To a stirred, ice-cold solution of sodium ethoxide in ethanol (prepared from 5.98 g of sodium spheres and 175 ml of ethanol) is added a solution of 29.8 g of thiophenol in 30 ml of ethanol during 15 min. After 10 min. this solution is treated at 0°-15° with a solution of 79.5 g of diethyl α-bromosuberate in 70 ml of ethanol during 15 min. The stirred mixture is warmed to room temperature during 60 min. and finally is heated at reflux for 60 min. The cooled solution is treated with 3 ml of gl acetic acid and concentrated. The residue is partitioned between ether and water. The ether layer is washed with water and brine, dried over MgSO4, and concentrated. The residue is subjected to fractional distillation to provide a light amber liquid, bp. 165°-180° (0.15 mm).

Workup

  1. temperaturefinally is heated
  2. temperatureat reflux for 60 min
  3. concentrationconcentrated
  4. customThe residue is partitioned between ether and water
  5. washThe ether layer is washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. distillationThe residue is subjected to fractional distillation
  9. customto provide a light amber liquid, bp. 165°-180° (0.15 mm)

Sources & evidence

ORD record
ord-0e1524980eb44ce4880e7ae85a87aa21
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

Loading…