4-Methylbenzenethiol → HCID 9928951, compound

HRID 2107142Notes

Reaction equation

HRID 2107142 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.Br[CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:13]([OH:15])=[O:14]>O.C(O)C>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:12]([S:10][C:7]2[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][CH:6]=2)[C:13]([OH:15])=[O:14])=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 78114-MethylbenzenethiolHCID 14798Sodium HydroxideHCID 23047782HCID 23047782, compound

Product 1

HCID 9928951HCID 9928951, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of 2.12 g (53 mmol) of caustic soda in 5 ml of water is added under nitrogen, at 0° C., to a solution of 3.27 g (26.3 mmol) of p-thiocresol in 50 ml of ethanol. Then a solution of 8.4 g (26.3 mmol) of 2-bromo-7-(4-chlorophenyl)heptanoic acid in 5 ml of ethanol is added and the cooling bath is removed. Then stirring is continued for 6 at room temperature; the mixture is let stand overnight and concentrated by evaporation. The residue is taken up in water, washed with ether and acidified with hydrochloric acid. The precipitated oil is extracted with methylene chloride. The extracts are dried and concentrated. The concentrate is chromatographed with a mixture of toluene and dioxane (5:1) on silica gel. Yield: 6.6 g (69% of theory) of 7-(4-chlorophenyl)-2-(4-methylphenylthio)heptanoic acid, M.P. 58°-61° C.

Workup

  1. customthe cooling bath is removed
  2. customis continued for 6 at room temperature
  3. concentrationconcentrated by evaporation
  4. washwashed with ether
  5. extractionThe precipitated oil is extracted with methylene chloride
  6. customThe extracts are dried
  7. concentrationconcentrated
  8. customThe concentrate is chromatographed with a mixture of toluene and dioxane (5:1) on silica gel

Sources & evidence

ORD record
ord-bb8e04ba723b4cbaa61dbb4bc53b1e7c
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

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