Methyl 2-(3-hydroxyprop-1-yn-1-yl)benzoate → Methyl 2-(3-hydroxypropyl)benzoate

HRID 368856Notes

Reaction equation

HRID 368856 reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[H][H]>CO.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 4321316Methyl 2-(3-hydroxyprop-1-yn-1-yl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 54370039Methyl 2-(3-hydroxypropyl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Step 2--A mixture of methyl o-(1-hydroxy-2-propyn-3-yl)benzoate (CXIX, 5.91 g) in methanol (60 ml) is hydrogenated at 40 psi hydrogen for 9 hrs using a total of 900 mg. Palladium on carbon (10%) is added in equal portions three times during the course of the reaction. The reaction is filtered and concentrated to give the saturated ester, methyl o-(1-hydroxyprop-3-yl)benzoate (CXXI).

Workup

  1. filtrationThe reaction is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e0de1580f71946f48cc1c4c8def22125
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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