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

HRID 844571Notes

Reaction equation

HRID 844571 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>C(O)(=O)C.[Pd]>[CH2:6]1[C:5]2[CH:4]=[CH:3][CH:2]=[C:1]([C:11]([OH:13])=[O:12])[C:10]=2[CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 1

HCID 68471-Naphthoic acid

Product 1

HCID 2396045,6,7,8-Tetrahydro-1-naphthalenecarboxylic acidYield 8.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

10% w/w Palladium-on-carbon (10 g) was added to a solution of 1-naphthoic acid (33.4 g) in glacial acetic acid (150 ml) and the mixture hydrogenated at 345 kPa (50 psi) and 85° C. for 4 days. The warm mixture was filtered through a short column of Arbacel (trade mark) filter aid and the pad washed with glacial acetic acid (150 ml). Water (1.5 L) was added to the filtrate and the resulting precipitate filtered off and washed with water. The precipitate was dissolved in dichloromethane, the solution dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give an oil which was crystallised from ethyl acetate to give 1,2,3,4-tetrahydro-5-naphthoic acid (2.94 g) as a white solid (m.p. 148-150° C.).

Workup

  1. filtrationThe warm mixture was filtered through a short column of Arbacel (trade mark)
  2. filtrationfilter aid
  3. washthe pad washed with glacial acetic acid (150 ml)
  4. additionWater (1.5 L) was added to the filtrate
  5. filtrationthe resulting precipitate filtered off
  6. washwashed with water
  7. dissolutionThe precipitate was dissolved in dichloromethane
  8. dry with materialthe solution dried over anhydrous sodium sulphate
  9. customthe solvent removed under reduced pressure
  10. customto give an oil which
  11. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-7d46c8385fc146c0aa6bb4f38f4fcfdd
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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