Methyl 3-hydroxynaphthalene-1-carboxylate → Methyl 3-hydroxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

HRID 2185886Notes

Reaction equation

HRID 2185886 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2>CC(O)=O.[Pd]>[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

4

Reactant 1

HCID 23423090Methyl 3-hydroxynaphthalene-1-carboxylate

Product 1

HCID 22452624Methyl 3-hydroxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylateYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 3-hydroxy-1-naphthalenecarboxylate (5.77 g, 28.5 mmol) and 10% Pd/C (1.57 g) in HOAc (140 mL) was hydrogenated on a Parr apparatus at 60° C., and 50 psi for 21 h. After filtration through a pad of diatomaceous earth the solvent was removed in vacuo and the residue treated with water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water, dried (MgSO4) and concentrated to yield product as a yellow oil (5.24 g, 89%). 1H NMR (CDCl3) δ 7.20 (d, 1H), 6.73 (d, 1H), 3.86 (s, 3H), 2.94 (d, 2H), 2.76 (d, 2H), 1.74 (m, 4H); MS m/z 205 (M−H).

Workup

  1. customwas hydrogenated on a Parr apparatus at 60° C.
  2. filtrationAfter filtration through a pad of diatomaceous earth the solvent
  3. customwas removed in vacuo
  4. additionthe residue treated with water
  5. extractionextracted with EtOAc (3×50 mL)
  6. washThe combined organic layers were washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-de61b2da1cf34201b226b577227f8808
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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