Sodium Hydroxide → HCID 68153641, compound

HRID 72985Notes

Reaction equation

HRID 72985 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][C:5]=1[CH2:14][OH:15])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[CH2:14][OH:15])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68290965HCID 68290965, compound

Product 1

HCID 68153641HCID 68153641, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-ethoxy-3-(hydroxymethyl)benzoate (1.6 g, 7.61 mmol) in dioxane (10 mL) was added NaOH (6.0 g, 37.5 mmol) and the reaction mixture was heated at 50° C. for 2 hours. The reaction mixture was concentrated in vacuo to half-volume, acidified to pH 2 with aq. 6N HCl solution. The resulting suspension was filtered, the solid rinsed with water and acetonitrile, then dried in vacuo to give 4-ethoxy-3-(hydroxymethyl)benzoic acid (740 mg, 50%) as a white solid. 1H NMR (400 MHz, DMSO) δ 12.51 (s, 1H), 8.00 (s, 1H), 7.81 (dd, J=8.5, 2.2 Hz, 1H), 7.01 (d, J=8.6 Hz, 1H), 5.13 (t, J=5.7 Hz, 1H), 4.50 (d, J=5.2 Hz, 2H), 4.11 (q, J=7.0 Hz, 2H), 1.34 (t, J=7.0 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to half-volume
  2. filtrationThe resulting suspension was filtered
  3. washthe solid rinsed with water and acetonitrile
  4. customdried in vacuo

Sources & evidence

ORD record
ord-56e62b06106f4d36b7df317514e5baac
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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