Ethanol → HCID 20297261, compound

HRID 1389616Notes

Reaction equation

HRID 1389616 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(Cl)(Cl)Cl.[OH-:27].[K+].S(=O)(=O)(O)O.[Cl-].[Na+].[CH2:36]([OH:38])C>>[C:16]1([S:22][CH:11]([C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=2)[C:36]([OH:38])=[O:27])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 7

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 6212ChloroformHCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 20297261HCID 20297261, compoundYield 77%

Conditions

Temperature
45 °C

Procedure

A mixture of 1.98 g (10 mmols) of 3-phenoxybenzaldehyde, 1.65 g (15 mmols) of thiophenol, 1.79 g (15 mmols) of chloroform and 2 ml of ethanol was stirred at room temperature (about 15° to 30° C.), and 10 ml of an ethanolic solution of 2.8 g (50 mmols) of potassium hydroxide was then added dropwise to the mixture while maintaining the temperature below 45° C. The reaction mixture was further stirred for an additional one hour at 45° C. and then allowed to stand overnight at room temperature while stirring. The reaction mixture was then poured into a mixture of 6 N sulfuric acid and ice clump to render the mixture acidic and then saturated with sodium chloride. The saturated solution was then extracted with diethyl ether and the extract was concentrated. The resulting concentrate was then charged into a silica gel column, and the column was eluted first with benzene-hexane (1:1 by volume) and then with hexane-ethyl acetate (4:1 by volume). The combined eluate was concentrated to obtain 2.58 g (77% yield) of 2-phenylthio-2-(3-phenoxyphenyl)acetic acid. NMR (CCl4) δ of Product: 4.68 (1H, s), 6.7-7.4 (14H, m), 11.6 (1H, bs).

Workup

  1. additionwas then added dropwise to the mixture
  2. temperaturewhile maintaining the temperature below 45° C
  3. waitto stand overnight at room temperature
  4. stirringwhile stirring
  5. extractionThe saturated solution was then extracted with diethyl ether
  6. concentrationthe extract was concentrated
  7. concentrationThe resulting concentrate
  8. additionwas then charged into a silica gel column
  9. washthe column was eluted first with benzene-hexane (1:1 by volume)
  10. concentrationThe combined eluate was concentrated

Sources & evidence

ORD record
ord-68e327d571774f4dbacddd652717454e
Source dataset
uspto-grants-1981_01
Patent number
US04245108

Reaction notes

Loading…