Methyl 2-(3-hydroxyprop-1-yn-1-yl)benzoate → Methyl 2-(3-hydroxypropyl)benzoate
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
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe reaction is filtered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-66d953c6b8164950a5d17ea13fda9dab
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877317
Reaction notes
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