Hydrochloric Acid → 3-[3-(3-Thienyl)phenoxy]propanal

HRID 1464770Notes

Reaction equation

HRID 1464770 reaction equation
C[O:2][CH:3](OC)[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:8]=1.Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[S:15]1[CH:16]=[CH:17][C:13]([C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[O:6][CH2:5][CH2:4][CH:3]=[O:2])=[CH:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 199170573-[3-(3-Thienyl)phenoxy] propanal dimethylacetal

Product 1

HCID 199171433-[3-(3-Thienyl)phenoxy]propanalYield 72.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.46 g of the resulting ether compound was dissolved in 5 ml of tetrahydrofuran, and 2 ml of 2N hydrochloric acid was added. The mixture was allowed to stand at room temperature for 4 hours, and then the solution was made basic with an aqueous solution of sodium bicarbonate. The solution was extracted with s ethyl acetate, and the extract was worked up in a customary manner. The product was purified by silica gel column chromatography [hexane / ethyl acetate =20/1→10/1] to give 0.28 g of 3-[3-(3-thienyl)phenoxy]propanal as a colorless oil.

Workup

  1. extractionThe solution was extracted with s ethyl acetate
  2. customThe product was purified by silica gel column chromatography [hexane / ethyl acetate =20/1→10/1]

Sources & evidence

ORD record
ord-a8f00bad64c44e53bba24d54a215b0c4
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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