Sodium Hydroxide → 4-(3-Hydroxypropoxy)-3-methyl-benzoic acid

HRID 72956Notes

Reaction equation

HRID 72956 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][C:7]=1[CH3:16].[OH-].[Na+]>O1CCOCC1>[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68291707Methyl 4-(3-hydroxypropoxy)-3-methyl-benzoate

Product 1

HCID 551336774-(3-Hydroxypropoxy)-3-methyl-benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 4-(3-hydroxypropoxy)-3-methyl-benzoate (0.9 g, 4.01 mmol) in dioxane (8 mL) was added 1N NaOH (5 mL) and the reaction mixture was heated at 70° C. for 22 hours. The solvent was concentrated in vacuo and the crude residue was dissolved in water (20 mL) and extracted with ethyl acetate (1×20 mL). The aqueous layer was acidified with 1 M HCl solution and extracted with ethyl acetate (2×20 mL). The organics were separated, dried with Na2SO4 and concentrated in vacuo to give 4-(3-hydroxypropoxy)-3-methyl-benzoic acid (0.7 g, 87%) as a white solid. ESI-MS m/z calc. 210.0. Found 211.0 (M+1)+; Retention time: 0.95 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 12.5 (bs, 1H), 7.97-7.60 (m, 2H), 7.01 (d, J=8.6 Hz, 1H), 4.57 (s, 1H), 4.11 (t, J=6.2 Hz, 2H), 3.59 (t, J=5.5 Hz, 2H), 2.19 (s, 3H), 1.89 (p, J=6.2 Hz, 2H).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. dissolutionthe crude residue was dissolved in water (20 mL)
  3. extractionextracted with ethyl acetate (1×20 mL)
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. customThe organics were separated
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eabbb487c2864544a2b077ffd811dc3a
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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