Chlorohydroquinone → Phenylpropynoic acid methyl ester

HRID 49689

Reaction equation

HRID 49689 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=[C:15]([OH:17])C=CC=1O.[CH3:18][OH:19]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]1([C:7]#[C:8][C:18]([O:17][CH3:15])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 301ChlorohydroquinoneHCID 887MethanolHCID 10821Phenylacetylene

Product 1

HCID 138378Phenylpropynoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A solution of phenylacetylene (10, 2 mmol), chlorohydroquinone(HQ-Cl) (0.4 mmol), molybdovanadophosphate (NPMoV) (35 mg) and palladium (II) acetate (50 mg) in methanol (10 mL) is stirred under CO/O2 (10 atm/0.5 atm) at 25° C. for 15 h. The reaction is then quenched with wet ether and the product is extracted with n-hexane. After removal of the solvent under reduced pressure, the product is isolated by column chromatography over silica gel (hexane:ethyl acetate 5:1) to give pure methyl phenylpropiolate.

Workup

  1. customThe reaction is then quenched with wet ether
  2. extractionthe product is extracted with n-hexane
  3. customAfter removal of the solvent under reduced pressure
  4. customthe product is isolated by column chromatography over silica gel (hexane:ethyl acetate 5:1)

Sources & evidence

ORD record
ord-1aebc336dba141bf826461f586cd7c39
Source dataset
uspto-grants-2004_03
Patent number
US06706927B2

Linked notes

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