1-Naphthoic acid → 5,6,7,8-Tetrahydro-1-naphthalenecarboxylic acid

HRID 976045Notes

Reaction equation

HRID 976045 reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>CC(O)=O.O=[Pt]=O>[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 68471-Naphthoic acid

Product 1

HCID 2396045,6,7,8-Tetrahydro-1-naphthalenecarboxylic acidYield 67%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 10.0 9 (0.058 mol) of 1-naphthoic acid in 100 mL HOAc was treated with 0.5 g PtO2 and reduced at 29° C., 50 psi. When the required amount of H2 had been taken up, the mixture was filtered and the solvent removed under reduced pressure. The residue was recrystallized from EtOAc/hexane to give 6.84 g (67% yield) of the product. The structure was confirmed by NMR spectroscopy.

Workup

  1. customreduced at 29° C.
  2. filtrationthe mixture was filtered
  3. customthe solvent removed under reduced pressure
  4. customThe residue was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-a33f016b8ece4c5391984057cfe8fb6e
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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