Potassium Hydroxide → HCID 58551608, compound

HRID 1908085Notes

Reaction equation

HRID 1908085 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])[C:7]([O:15][CH3:16])=[CH:6][C:3]=1[CH:4]=[O:5].[OH-].[K+].[O-:19][Mn](=O)(=O)=O.[K+]>O1CCOCC1>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])[C:7]([O:15][CH3:16])=[CH:6][C:3]=1[C:4]([OH:19])=[O:5]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 58086339HCID 58086339, compound

Product 1

HCID 58551608HCID 58551608, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Fluoro-5-methoxy-4-(2-methoxyethoxy)benzaldehyde (0.36 g, 1.6 mmol) was suspended in a mixture of dioxane (1.5 mL) and KOH (16 mL of 0.2 M, 3.2 mmol). KMnO4 (370 mg, 2.4 mmol) was added and the mixture was stirred vigorously for 30 minutes. The reaction mixture was filtered and the filtrate was concentrated to 10 mL (blue soln). HCl (4M, ˜2 mL) was added and the resulting precipitate was filtered and washed with 1M HCl and then water (1 mL) to yield 2-fluoro-5-methoxy-4-(2-methoxyethoxy)benzoic acid (300 mg, 78%) as a white solid. ESI-MS m/z calc. 244.1. found 245.1 (M+1)+. Retention time: 1.01 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 12.96 (s, 1H), 7.30 (d, J=7.0 Hz, 1H), 6.98 (d, J=12.5 Hz, 1H), 4.20-4.13 (m, 2H), 3.78 (s, 3H), 3.71-3.63 (m, 2H), 3.31 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to 10 mL (blue soln)
  3. additionHCl (4M, ˜2 mL) was added
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with 1M HCl

Sources & evidence

ORD record
ord-56341215b8d746c7aa152963d172b46d
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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