Hydrochloric Acid → HCID 23050491, compound

HRID 1651798Notes

Reaction equation

HRID 1651798 reaction equation
C(OC([O:6][CH2:7][C:8]#[C:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[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]([O:18][CH3:19])=[CH:16][CH:17]=1)=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23050495HCID 23050495, compound

Product 1

HCID 23050491HCID 23050491, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.3 g (27.8 mmol) of 4-(1-ethoxyethoxy)-1-(4-methoxyphenyl)-2-butyn-1-one in 95 ml of tetrahydrofuran was treated at room temperature with 28 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 methylene chloride/hexane yielded 4-hydroxy-1-(4-methoxyphenyl)-2 -butyn-1-one of melting point 84°-85°.

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 methylene chloride/hexane

Sources & evidence

ORD record
ord-4cda0db9b2bb4de8a582ed06b1e260a3
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

Loading…