Hydrochloric Acid → HCID 23050465, compound

HRID 1651794Notes

Reaction equation

HRID 1651794 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[C:13](=[O:17])[C:14]#[C:15][CH3:16].Cl.[O:19]1CCCC1>>[OH:19][CH2:16][C:15]#[C:14][C:13]([C:4]1[CH:5]=[CH:6][C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1])=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 86743984HCID 86743984, compound

Product 1

HCID 23050465HCID 23050465, compound

Procedure

A solution of 8.3 g (27.6 mmol) of 4-1-ethoxytehoxy)- 1-(2,3.4-trimethoxyphenyl)-2 -butyn-1-one in 95 ml of tetrahydrofuran was treated at room temperature with 27.5 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-(2,3,4 -trimethoxyphenyl)-2-butyn-1-one of melting point 82°-83°.

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-78cb5f322cc44589ac25d453404072e7
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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