Sodium Hydroxide → beta-Phenylisovaleric acid

HRID 439338Notes

Reaction equation

HRID 439338 reaction equation
[OH-:1].[Na+].BrBr.[CH3:5][C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH2:7][C:8](=[O:10])C>>[CH3:11][C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:5])[CH2:7][C:8]([OH:10])=[O:1]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 818982-Pentanone, 4-methyl-4-phenyl-

Product 1

HCID 13890beta-Phenylisovaleric acid

Procedure

To a solution of NaOH (47.2 g, 1.18 mole) in ice/H2O (270 g) maintained at 4°-5° C. was added Br2 (68.7 g, 0.43 mole) followed by 4-methyl-4-phenyl-2-pentanone (23.7 g, 0.135 mole). The reaction was stirred for 18 hours at room temperature. The crude reaction mixture was extracted with CCl4 (discarded), acidified to pH 1-2 with concentrated HCl solution and extracted with ethyl acetate. The combined organics were washed with saturated NaCl solution, dried over Na2SO4 and evaporated in vacuo to obtain 22.5 g of the title B compound as an off-white solid. This was used in the next step without further purification. MS: (M+NH4)+ @ 196.

Workup

  1. customThe crude reaction mixture
  2. extractionwas extracted with CCl4 (discarded)
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with saturated NaCl solution
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customto obtain 22.5 g of the title B compound as an off-white solid
  8. customThis was used in the next step without further purification

Sources & evidence

ORD record
ord-fa103291c50e42f18756346688f8f844
Source dataset
uspto-grants-1996_05
Patent number
US05514690

Reaction notes

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