3-Hydroxy-2-naphthoic acid → 25435-10-3

HRID 2185877Notes

Reaction equation

HRID 2185877 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2>[Pd].C(O)(=O)C>[OH:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

4

Reactant 1

HCID 71043-Hydroxy-2-naphthoic acid

Product 1

HCID 2259274225435-10-3Yield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-hydroxy-2-naphthalenecarboxylic acid (15.0 g, 0.08 moles), 10% Pd/C (4.46 g) and acetic acid (190 mL) was hydrogenated at 60° C. and 50 psi for 7 h. The cooled reaction mixture was filtered through diatomaceous earth and washed with ethanol (4×25 mL). The yellow filtrate was concentrated in vacuo to afford 13.82 g (91%) of a purple solid. 1H NMR (CDCl3) δ 7.61 (s, 1H), 6.71 (s, 1H), 2.74 (d, 4H), 1,78 (s, 4H). MS m/z 191 (M−H).

Workup

  1. customwas hydrogenated at 60° C.
  2. customThe cooled reaction mixture
  3. filtrationwas filtered through diatomaceous earth
  4. washwashed with ethanol (4×25 mL)
  5. concentrationThe yellow filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2926fd6c432e4b9f8ffb790343ccb1aa
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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