Hydrochloric Acid → 1-[5-Hydroxy-2-(phenylethynyl)phenyl]-2-propanone

HRID 2291904Notes

Reaction equation

HRID 2291904 reaction equation
C([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:9]([CH2:11][C:12](=[O:14])[CH3:13])[CH:10]=1)(=O)C.[OH-].[Na+].Cl>CO>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([C:15]#[C:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:9]([CH2:11][C:12](=[O:14])[CH3:13])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 212782901-[5-Acetoxy-2-(phenylethynyl)phenyl]-2-propanone

Product 1

HCID 212782891-[5-Hydroxy-2-(phenylethynyl)phenyl]-2-propanoneYield 101%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-[5-Acetoxy-2-(phenylethynyl)phenyl]-2-propanone (3.3 g, 11 mmole) was dissolved in MeOH (15 mL) and treated with 50% sodium hydroxide solution (1.8 g, 22 mmole) under argon. The reaction was stirred for 1 hr then poured into dilute hydrochloric acid and extracted with diethyl ether. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The product was dried under vacuum to yield 2.78 g (98%) of the title compound.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-d5c60c1579594ad2a2cbc52e098f12ea
Source dataset
uspto-grants-1989_01
Patent number
US04798893

Reaction notes

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