Sodium Hydroxide → 3-(Benzyloxy)-2,2-dimethylpropanoic acid

HRID 1919414Notes

Reaction equation

HRID 1919414 reaction equation
[OH-].[Na+].[CH3:3][C:4]([CH3:18])([CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([O:7]C)=[O:6]>O1CCCC1.CO.Cl.C(OCC)(=O)C>[CH3:3][C:4]([CH3:18])([CH2:9][O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 59267989Methyl 3-(benzyloxy)-2,2-dimethylpropanoate

Product 1

HCID 134782883-(Benzyloxy)-2,2-dimethylpropanoic acidYield 93%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Adapting procedures or variations thereof according to Rega et al., Eur. J. Org. Chem. 2007, 6, 934-942; Woo et al., J. Org. Chem. 2004, 69(25), 8984-8986; and Abiko et al., Tetrahedron Lett 1986, 27(38), 4537-40, 3.4 mL of an ten molar (10 M) aqueous solution of sodium hydroxide (NaOH) (34.0 mmol) was added to a solution of 3.7 g (16.9 mmol) of methyl-2,2-dimethyl-3-(phenylmethoxy)propanoate (26a) in a mixture of 15 mL of tetrahydrofuran (THF) and 5 mL of methanol (MeOH). The solution was vigorously stirred overnight at room temperature. Upon completion of the reaction, the reaction mixture was further diluted with one molar (1.0 M) hydrochloric acid (HCl) and ethyl acetate (EtOAc) and the phases were separated. The aqueous phase was extracted two additional times with ethyl acetate (EtOAc) and the combined organic extracts were washed with brine. The organic solution was dried over anhydrous magnesium sulfate (MgSO4), filtered, and the solvents and benzyl alcohol were removed under reduced pressure using a rotary evaporator. The crude material was used in the next step without further purification. Three-point-three (3.3) g (93% yield) of the title compound (26b) was obtained as a colorless solid. 1H NMR (400 MHz, CDCl3): δ=1.10 (s, 6H), 3.40 (s, 2H), 4.47 (s, 2H), 7.26-7.35 (m, 5H) ppm. The analytical data was consistent with the proposed structure.

Workup

  1. customUpon completion of the reaction
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted two additional times with ethyl acetate (EtOAc)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialThe organic solution was dried over anhydrous magnesium sulfate (MgSO4)
  6. filtrationfiltered
  7. customthe solvents and benzyl alcohol were removed under reduced pressure
  8. customa rotary evaporator
  9. customThe crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-a2d05124962d44a3874315264a8f2110
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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