Potassium Hydroxide → (3-Thien-3-ylphenyl)methanol

HRID 2295849Notes

Reaction equation

HRID 2295849 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:16]=[CH:15][S:14][CH:13]=2)[CH:7]=1)(=O)C.[OH-].[K+]>CO>[S:14]1[CH:15]=[CH:16][C:12]([C:8]2[CH:7]=[C:6]([CH2:5][OH:4])[CH:11]=[CH:10][CH:9]=2)=[CH:13]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 1324342189929-86-2

Product 1

HCID 7164662(3-Thien-3-ylphenyl)methanolYield 105.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3.3 g (0.014 mol) of 3-(3-thienyl)phenylmethyl acetate was added with stirring a solution of 1.4 g (0.021 mol) of potassium hydroxide in 100 mL of methanol. The reaction mixture was stirred at ambient temperature for 19 hours. The volume of the reaction mixture was reduced to to 30 mL by concentration under reduced pressure. The concentrate was placed in a separatory funnel, and 100 mL of a saturated aqueous solution of sodium chloride was added. The mixture was extracted with five portions of 60 mL each of methylene chloride. The extracts were combined and washed with 200 mL of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a residual oil. The oil was subjected to column chromatography on silica gel, eluting with toluene:pentane (3:2). The appropriate fractions were combined to give 2.8 g of 3-(3-thienyl)phenylmethanol.

Workup

  1. concentrationThe volume of the reaction mixture was reduced to to 30 mL by concentration under reduced pressure
  2. customThe concentrate was placed in a separatory funnel
  3. addition100 mL of a saturated aqueous solution of sodium chloride was added
  4. extractionThe mixture was extracted with five portions of 60 mL each of methylene chloride
  5. washwashed with 200 mL of a saturated aqueous solution of sodium chloride
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customto give a residual oil
  10. washeluting with toluene:pentane (3:2)

Sources & evidence

ORD record
ord-058f16f2ce4e4e1b911a128640b11ed3
Source dataset
uspto-grants-1984_01
Patent number
US04426524

Reaction notes

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