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Hydrochloric Acid → 2-[(Para-benzyl)-phenoxy]-2-methyl-propionic acid

HRID 1448056
Notes
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Reaction equation

HRID 1448056 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.C[Mg]I.[C:18](#N)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>C1COCC1>[CH2:18]([C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7505BenzonitrileHCID 3448942-(4-Bromophenoxy)-2-methylpropanoic acidHCID 178418373HCID 178418373, compound

Product 1

HCID 537591862-[(Para-benzyl)-phenoxy]-2-methyl-propionic acidYield 77%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

26 g (0.1 mole) of 2-[(para-bromo)-phenoxy]-2-methyl-propionic acid is dissolved in 200 cc of anhydrous THF and placed in a 500 cc flask. The mixture is cooled in an ice bath and 0.2 mole of methylmagnesium iodide (prepared in solution of THF) is added slowly. After this addition, the temperature is allowed to rise and the mixture stirred at ambient temperature for 11/2 hours. Then slowly and drop by drop a solution of 4.1 g (0.1 mole) of benzonitrile in 20 cc of THF is added and the mixture is stirred for 2 hours 30 minutes at ambient temperature. The reaction mixture is poured on to 500 cc of 10% hydrochloric acid, cooled by 500 g of ice, and vigorously stirred. The reaction mixture is extracted with ether and the ethereal phases are washed, dried and decolorised. The ether solvent is evaporated under vacuum and the oily residue placed in a desiccator under vacuum. 2-[(para-benzoyl)-phenoxy]-2-methylpropionic acid slowly crystallises (22 g). The yield is 77% and the melting point 130° C.

Workup

  1. customplaced in a 500 cc flask
  2. temperatureThe mixture is cooled in an ice bath
  3. additionAfter this addition
  4. additionis added
  5. stirringthe mixture is stirred for 2 hours 30 minutes at ambient temperature
  6. stirringvigorously stirred
  7. extractionThe reaction mixture is extracted with ether
  8. washthe ethereal phases are washed
  9. customdried
  10. customThe ether solvent is evaporated under vacuum
  11. customthe oily residue placed in a desiccator under vacuum
  12. custom2-[(para-benzoyl)-phenoxy]-2-methylpropionic acid slowly crystallises (22 g)

Sources & evidence

ORD record
ord-a08d466fe9d049e5ba452ff75161b687
Source dataset
uspto-grants-1979_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04179515

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes