Ethanol → 5-Cyano-2-hydroxybenzoic acid

HRID 644401Notes

Reaction equation

HRID 644401 reaction equation
C(O)C.C([O:11][C:12](=[O:29])[C:13]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][C:14]=1[O:21]CC1C=CC=CC=1)C1C=CC=CC=1>[Pd].O1CCCC1>[C:19]([C:17]1[CH:18]=[C:13]([C:12]([OH:29])=[O:11])[C:14]([OH:21])=[CH:15][CH:16]=1)#[N:20]

Participants

5

Reactant 2

HCID 702EthanolHCID 18974028Benzyl 2-benzyloxy-5-cyanobenzoate

Product 1

HCID 130269355-Cyano-2-hydroxybenzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethanol (10 mL) and tetrahydrofuran (10 mL) were added to 2-benzyloxy-5-cyanobenzoic acid benzyl ester (446 mg, 1.3 mmol) and 5% palladium on carbon (45 mg), and the mixture was hydrogenated at room temperature for 2 hours. After the insoluble matter was filtered off, the solvent was evaporated under reduced pressure to give the title compound (212 mg, 100.0%) as a white solid.

Workup

  1. filtrationAfter the insoluble matter was filtered off
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-eab15355bce64c8bbc10a08fb4923ec7
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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