Potassium Hydroxide → HCID 19788163, compound

HRID 1656480Notes

Reaction equation

HRID 1656480 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:18])[C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH2:13][O:14]C(=O)C)[CH:7]=1>CO.O>[OH:14][CH2:13][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([CH3:12])[CH:9]=1)[C:5]([OH:18])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19788165HCID 19788165, compound

Product 1

HCID 19788163HCID 19788163, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

In a 5 liter flask were dissolved 380 g (5.77 mole) of 85% KOH in 2.2 liter of methanol and warmed up to 60° C. The methyl-3-acetoxymethyl-5-methylbenzoate from the previous step was added and heated with stirring at 60° C. for 2.5 hrs. The reaction mixture was cooled down to room temperature and the solvent eliminated in the rotavap. The resulting oil was dissolved in 1.5 liter of water and then washed with ethyl ether (1×1 liter). The aqueous layer was made acidic with concentrated hydrochloric acid and the resulting acidic suspension was extracted with ethyl acetate (3×350 ml). The combined organic extracts were then washed with water (2×600 ml) and then brine (2×500 ml), dried over sodium sulfate and concentrated in the rotavap to give 287.6 g of 3-hydroxymethyl-5-methylbenzoic acid.

Workup

  1. temperatureheated
  2. temperatureThe reaction mixture was cooled down to room temperature
  3. washwashed with ethyl ether (1×1 liter)
  4. extractionthe resulting acidic suspension was extracted with ethyl acetate (3×350 ml)
  5. washThe combined organic extracts were then washed with water (2×600 ml)
  6. dry with materialbrine (2×500 ml), dried over sodium sulfate
  7. concentrationconcentrated in the rotavap

Sources & evidence

ORD record
ord-c046b336c35d4d9f852a7ea97be6d872
Source dataset
uspto-grants-1993_10
Patent number
US05254584

Reaction notes

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