Water → 89929-86-2

HRID 2295848Notes

Reaction equation

HRID 2295848 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[C:14]([O-:17])(=[O:16])[CH3:15].[K+].O>C(O)(=O)C>[C:14]([O:17][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:4]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 517044Potassium AcetateHCID 132459263-[3-(Bromomethyl)phenyl]thiophene

Product 1

HCID 1324342189929-86-2Yield 41.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred solution of 8.7 g (0.034 mol) of 3-(3-bromomethylphenyl)thiophene and 5.1 g (0.051 mol) of potassium acetate in 65 mL of glacial acetic acid was heated under reflux for three hours. The reaction mixture was cooled and transferred to a separatory funnel, and 150 mL of water was added. The mixture was extracted with two portions of 120 mL each of methylene chloride. The combined extracts were washed with 150 mL of a saturated solution of sodium chloride, two portions of 150 mL each of a saturated aqueous solution of sodium bicarbonate, and finally 100 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 an oil residue. The residue was subjected to column chromatography on silica gel, eluting with hexane:methylene chloride (3:2). The appropriate fractions were combined to give 3.3 g of 3-(3-thienyl)phenylmethyl acetate.

Workup

  1. temperatureunder reflux for three hours
  2. temperatureThe reaction mixture was cooled
  3. customtransferred to a separatory funnel
  4. extractionThe mixture was extracted with two portions of 120 mL each of methylene chloride
  5. washThe combined extracts were washed with 150 mL of a saturated solution of sodium chloride, two portions of 150 mL each of a saturated aqueous solution of sodium bicarbonate, and finally 100 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 an oil residue
  10. washeluting with hexane:methylene chloride (3:2)

Sources & evidence

ORD record
ord-9f1a8cef54b348c4a72d7731de5987b2
Source dataset
uspto-grants-1984_01
Patent number
US04426524

Reaction notes

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