Benzyl 4-(methoxycarbonylmethoxy)benzoate → 4-(2-Methoxy-2-oxoethoxy)benzoic acid
Reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[CH:22]=[CH:21][C:10]([C:11]([O:13]CC2C=CC=CC=2)=[O:12])=[CH:9][CH:8]=1)=[O:4]>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[CH:22]=[CH:21][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)=[O:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
5 g of benzyl 4-(methoxycarbonylmethyloxy)benzoate were dissolved in methanol/ethyl acetate and hydrogenated in the presence of 600 mg of catalyst (Pd/C, 10% strength). After flushing with inert gas, the catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was triturated with diisopropyl ether/heptane (9/1) and filtered off with suction. Yield: 3.3 g.
Workup
- customAfter flushing with inert gas
- filtrationthe catalyst was filtered off
- concentrationthe filtrate was concentrated in vacuo
- customThe residue was triturated with diisopropyl ether/heptane (9/1)
- filtrationfiltered off with suction
Sources & evidence
- ORD record
- ord-98e91f9d14c84c1d8174fa981c6ece30
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06492356B1
Reaction notes
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