Hydrochloric Acid → HCID 23050499, compound

HRID 1651796Notes

Reaction equation

HRID 1651796 reaction equation
C(OC([O:6][CH2:7][C:8]#[C:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)=[O:11])C)C.Cl>O1CCCC1>[OH:6][CH2:7][C:8]#[C:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23050522HCID 23050522, compound

Product 1

HCID 23050499HCID 23050499, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.7 g (23 mmol) of 4-(1-ethoxyethoxy)-1-(4-methylphenyl)-2-butyn-1-one in 80 ml of tetrahydrofuran was treated at room temperature with 23 ml of 2N hydrochloric acid, whereupon the mixture was stirred for 30 minutes. The reaction mixture was then extracted twice with ethyl acetate. The combined organic phases were washed in succession with saturated sodium carbonate solution and with water, dried over magnesium sulphate and concentrated. Crystallization of the residue from ethyl acetate/hexane yielded 4-hydroxy-1-(4-methylphenyl)-2-butyn-1-one of melting point 74°.

Workup

  1. extractionThe reaction mixture was then extracted twice with ethyl acetate
  2. washThe combined organic phases were washed in succession with saturated sodium carbonate solution and with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customCrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-836fb3d797764d3a8849bf6e129322ed
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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