Hydrochloric Acid → HCID 23050457, compound

HRID 1651797Notes

Reaction equation

HRID 1651797 reaction equation
C(OC([O:6][CH2:7][C:8]#[C:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[O:11])C)C.Cl>O1CCCC1>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[C:9]#[C:8][CH2:7][OH:6])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23050451HCID 23050451, compound

Product 1

HCID 23050457HCID 23050457, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.3 g (29 mmol) of 4-(1-ethoxyethoxy)-1-(4-fluorophenyl)-2-butyn-1-one in 100 ml of tetrahydrofuran was treated at room temperature with 29 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 1-(4-fluorophenyl)-4-hydroxy-2-butyn-1-one of melting point 63°.

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-838f460154294da0939ff402d5226666
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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