Hydrochloric Acid → HCID 23051866, compound

HRID 1651362Notes

Reaction equation

HRID 1651362 reaction equation
C(OC([O:6][CH2:7][C:8]#[C:9][C:10](=[O:21])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)C)C.Cl>O1CCCC1.O>[OH:6][CH2:7][C:8]#[C:9][C:10](=[O:21])/[CH:11]=[CH:12]/[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 23051873HCID 23051873, compound

Product 1

HCID 23051866HCID 23051866, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3 g (10.4 mmol) of (E)-6-(1-ethoxy-ethoxy)-1-(4-methoxyphenyl)-1-hexen-4-yn-3-one in 50 ml of tetrahydrofuran was treated at room temperature with 3 ml of 1N hydrochloric acid and stirred at room temperature for 30 minutes. The reaction mixture was diluted with water and extracted twice with ether. The combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by flash chromatography on 100 g of silica gel (elution agent methylene chloride/ether 4:1) and was subsequently crystallized from methylene chloride/ether/hexane. There was obtained (E)-6-hydroxy-1-(4-methoxyphenyl)-1-hexen-4-yn-3-one of melting point 68°-69°.

Workup

  1. extractionextracted twice with ether
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on 100 g of silica gel (elution agent methylene chloride/ether 4:1)
  5. customwas subsequently crystallized from methylene chloride/ether/hexane

Sources & evidence

ORD record
ord-d89c362a825440e99a49044243dd3dd4
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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