2-Methoxy-1-naphthoic acid → HCID 22452625, compound

HRID 2185893Notes

Reaction equation

HRID 2185893 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:13]([OH:15])=[O:14]>CC(O)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 703562-Methoxy-1-naphthoic acid

Product 1

HCID 22452625HCID 22452625, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-methoxy-1-naphthalenecarboxylic acid (1.0 g, 4.95 mmol) and 10% Pd/C (0.3 g) in HOAc (25 mL) was hydrogenated on Parr apparatus at 60° C. and 50 psi for 23 h. After filtration through diatomaceous earth, the solvent was removed under reduced pressure, and water was added. The solid was filtered and washed with water to give product as a yellow solid (0.377 g, 37%). 1H NMR (DMSO-d6) δ 12.81 (s, 1H), 7.05 (d, 1H), 6.83 (d, 1H), 3.68 (s, 3H), 2.66 (s, 2H), 2.59 (s, 2H), 1.69 (m, 4H); MS m/z 205 (M−H).

Workup

  1. customwas hydrogenated on Parr apparatus at 60° C.
  2. filtrationAfter filtration through diatomaceous earth
  3. customthe solvent was removed under reduced pressure, and water
  4. additionwas added
  5. filtrationThe solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-26cb02b6156c457fbd1aeb10b536344f
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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