HCID 22452664, compound → HCID 22452628, compound

HRID 2185905Notes

Reaction equation

HRID 2185905 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:15]([OH:17])=[O:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)([CH3:3])[CH3:2]>CC(O)=O.[Pd]>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:15]([OH:17])=[O:16])[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[CH:14]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 22452664HCID 22452664, compound

Product 1

HCID 22452628HCID 22452628, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-(isopropoxy)-1-naphthalenecarboxylic acid (0.38 g, 1.65 mmol) and 10% Pd/C (0.10 g) in HOAc (20 mL) was hydrogenated on Parr apparatus at 60° C. and 50 psi for 13 h. After filtration through diatomaceous earth the solvent was removed in vacuo, water was added and the precipitate was extracted into EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated to yield the title acid as a light yellow oil (0.39 g, 100%). 1H NMR (CDCl3) δ 7.39 (d, 1H), 6.83 (d, 1H), 4.55 (m, 1H), 3.02 (s, 2H), 2.80 (s, 2H), 1.77 (m, 4H), 1.34 (s, 3H), 1.32 (s, 3H); MS m/z 233 (M−H).

Workup

  1. customwas hydrogenated on Parr apparatus at 60° C.
  2. filtrationAfter filtration through diatomaceous earth the solvent
  3. customwas removed in vacuo, water
  4. additionwas added
  5. extractionthe precipitate was extracted into EtOAc
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-393d04bbbaa14af7be5f1b6adc18c252
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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