Methyl 2-hydroxy-1-naphthoate → Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate

HRID 631876

Reaction equation

HRID 631876 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[OH:15])=[O:4].[H][H]>C(O)(=O)C.[Pt]=O>[CH3:1][O:2][C:3]([C:5]1[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[CH:7][C:6]=1[OH:15])=[O:4]

Participants

5

Reactant 2

HCID 598533Methyl 2-hydroxy-1-naphthoateHCID 178418361HCID 178418361, compound

Product 1

HCID 11600901Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylateYield 114.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Under an atmosphere of nitrogen, platinum oxide (5 g) was added to a solution of 2-hydroxy-naphthalene-1-carboxylic acid methyl ester (10 g) in acetic acid (200 mL). The nitrogen atmosphere was replaced by hydrogen, the pressure was increased to 4 bar and the mixture was stirred overnight. The resulting suspension was filtered and the filtrate was concentrated under vacuum to give an oil. The residue was purified by chromatography on silica, eluting with DCM. The fractions containing the desired product were combined and evaporated under vacuum to give the title compound as a colorless oil (11.7 g).

Workup

  1. temperaturethe pressure was increased to 4 bar
  2. filtrationThe resulting suspension was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. customto give an oil
  5. customThe residue was purified by chromatography on silica
  6. washeluting with DCM
  7. additionThe fractions containing the desired product
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-eaa2476de1ea47278ce680562c721a0d
Source dataset
uspto-grants-2016_04
Patent number
US09321740B2

Linked notes

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