Hydrochloric Acid → 2-[4-(2-Carboxy-2-methylpropyl)phenoxymethyl]benzoic acid

HRID 1417102Notes

Reaction equation

HRID 1417102 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:30])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([C:25]([O:27]CC)=[O:26])([CH3:24])[CH3:23])=[CH:17][CH:16]=1)C.Cl>C(O)C.O>[C:25]([C:22]([CH3:24])([CH3:23])[CH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([OH:30])=[O:5])=[CH:16][CH:17]=1)([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 67599519HCID 67599519, compound

Product 1

HCID 675986322-[4-(2-Carboxy-2-methylpropyl)phenoxymethyl]benzoic acidYield 91.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution containing 30.2 g of potassium hydroxide in 150 ml 95% ethanol was added to 2-[4-(2-ethoxycarbonyl-2-methylpropyl)phenoxymethyl]benzoic acid ethyl ester (20.3 g) and warmed to reflux for 8 hours. The solution was cooled, diluted with water and adjusted to pH 5 with 6N HCl. Cooling overnight gave a precipitate which was collected and air dried to give 15.9 g of 2-[4-(2-carboxy-2-methylpropyl)phenoxymethyl]benzoic acid as a powder.

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 8 hours
  3. temperatureThe solution was cooled
  4. temperatureCooling overnight
  5. customgave a precipitate which
  6. customwas collected
  7. customair dried

Sources & evidence

ORD record
ord-726318891d80418ba51d5228bfa4e519
Source dataset
uspto-grants-1999_06
Patent number
US05917057

Reaction notes

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