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

HRID 259010

Reaction equation

HRID 259010 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[H][H]>[Pd].C(O)(=O)C>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 598533Methyl 2-hydroxy-1-naphthoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11600901Methyl 2-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

In 2.5 l. of glacial acetic acid is dissolved 417 g. of methyl 2-hydroxy-1-naphthoate, and with the addition of 150 g. of 5% palladium-on-carbon, reduction is carried out at a temperature of 60° to 80° C with hydrogen introduced at a pressure of 100kg./cm2. In 3 hours, approximately 2 moles of hydrogen is absorbed. The reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is then subjected to distillation under reduced pressure and the fraction boiling at 123° -125° C (0.6 mmHg) is recovered to obtain methyl 2-hydroxy-5,6,7,8-tetrahydro-1-naphthoate as a colorless oil. The oil solidifies on standing in the cold.

Workup

  1. additionintroduced at a pressure of 100kg
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. distillationThe residue is then subjected to distillation under reduced pressure
  5. customthe fraction boiling at 123° -125° C (0.6 mmHg) is recovered

Sources & evidence

ORD record
ord-2126f8ab992c4dcc9337b56ee47aa1d9
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Linked notes

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