Potassium Hydroxide → 4-Tert-butoxy-3-methoxy-benzoic acid

HRID 72926Notes

Reaction equation

HRID 72926 reaction equation
[C:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][C:7]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[O-:18][Mn](=O)(=O)=O.[K+]>O1CCOCC1>[C:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]([OH:18])=[O:11])=[CH:8][C:7]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 516875Potassium PermanganateHCID 154394174-Tert-butoxy-3-methoxybenzaldehyde

Product 1

HCID 585512294-Tert-butoxy-3-methoxy-benzoic acidYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-tert-Butoxy-3-methoxybenzaldehyde (130 mg, 0.62 mmol) was suspended in a mixture of dioxane (520 μL) and potassium hydroxide (6.5 mL of 0.20 M, 1.3 mmol). KMnO4 (150 mg, 0.93 mmol) was added and the reaction was stirred vigorously for 16 hours. The reaction mixture was filtered and then concentrated in vacuo to 3 mL. Hydrochloric acid (1M, 4 mL) was added and the resulting precipitate was filtered and washed with 1M HCl and a small amount of water to yield 4-tert-butoxy-3-methoxy-benzoic acid (68 mg, 49%) as a white solid. ESI-MS m/z calc. 224.1. Found 225.2 (M+1)+. Retention time: 1.66 minutes (3 min run). 1H NMR (400 MHz, DMSO) δ 12.80 (s, 1H), 7.66-7.41 (m, 2H), 7.09 (d, J=8.8 Hz, 1H), 3.78 (s, 3H), 1.32 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo to 3 mL
  3. additionHydrochloric acid (1M, 4 mL) was added
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with 1M HCl

Sources & evidence

ORD record
ord-d3fbef197dd8450cae04c60c45e5503a
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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