Hydrochloric Acid → 3-Methyl-4-propoxybenzoic acid

HRID 713086Notes

Reaction equation

HRID 713086 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH3:17])[C:5]([O:7]CCC)=[O:6].O.[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH3:17])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68291556Propyl 3-methyl-4-propoxybenzoate

Product 1

HCID 627024243-Methyl-4-propoxybenzoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

The crude propyl 3-methyl-4-propoxybenzoate was dissolved in methanol (25 mL) and water (50 mL) and treated with solid sodium hydroxide (31.6 g, 789 mmol). The reaction mixture was refluxed for 1 h. The reaction mixture cooled to 0° C. and acidified with 12 M HCl (74 mL, 890 mmol). The resulting solid filtered to provide 3-methyl-4-propoxybenzoic acid (3.22 g, 16.6 mmol, 84%) as a light pink solid. ESI-MS m/z calc. 194.0943. found 195.3 (M+1)+; Retention time: 1.41 minutes (3 min run). 1H NMR (400 MHz, DMSO-d6) δ 12.50 (s, 1H), 7.77 (dd, J=8.5, 2.2 Hz, 1H), 7.73 (d, J=1.4 Hz, 1H), 6.99 (d, J=8.6 Hz, 1H), 4.01 (t, J=6.4 Hz, 2H), 2.18 (s, 3H), 1.82-1.69 (m, 2H), 1.01 (t, J=7.4 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. filtrationThe resulting solid filtered

Sources & evidence

ORD record
ord-bccfbac10cf245519c3d95842b405165
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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