Acetic Acid → 1033845-00-9

HRID 602115Notes

Reaction equation

HRID 602115 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][N:9]=1.[OH-].[Na+].C(O)(=O)C>O1CCOCC1>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 136360163HCID 136360163, compound

Product 1

HCID 1357414751033845-00-9Yield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 6-(2-hydroxyphenyl)nicotinate (1.13 g, 4.9 mmol) was dissolved in 1,4-dioxane (10.0 ml) and 1N aqueous NaOH (12.0 ml) added. The resulting solution was stirred at r.t. for 16 h. This solution was then acidified to pH 4-5 with glacial acetic acid and concentrated under reduced pressure to 5 ml volume. This solution was diluted with water (30 ml) and the resulting precipitate filtered, washed with water (10 ml) and dried to give the title compound as a yellow solid (0.77 g) (72%). 1H NMR (400 MHz, DMSO-d6) □ ppm 9.07 (1H, s), 8.39-8.34 (1H, m), 8.30-8.25 (1H, m), 8.06-7.99 (1H, m), 7.36-7.29 (1H, m), 6.96-6.89 (2H, m). LRMS: ES m/z 216 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure to 5 ml volume
  2. additionThis solution was diluted with water (30 ml)
  3. filtrationthe resulting precipitate filtered
  4. washwashed with water (10 ml)
  5. customdried

Sources & evidence

ORD record
ord-5b5ce6573765475e8a6865a462f6021a
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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