Carbon Dioxide → 4-(Benzyloxy)-2-ethylbenzoic acid

HRID 2220609Notes

Reaction equation

HRID 2220609 reaction equation
C([Li])CCC.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[C:16]([CH2:21][CH3:22])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:23](=[O:25])=[O:24].O>CCCCCC.O1CCCC1.C1(C)C=CC=CC=1>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:23]([OH:25])=[O:24])=[C:16]([CH2:21][CH3:22])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 151434711-Bromo-2-ethyl-4-[(phenylmethyl)oxy]benzeneHCID 178418339Butyllithium

Product 1

HCID 231341484-(Benzyloxy)-2-ethylbenzoic acidYield 51.1%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

A 1.59 mol/L solution of n-butyllithium in n-hexane (2.28 mL) was added to a solution of 4-benzyloxy-1-bromo-2-ethylbenzene (0.96 g) in tetrahydrofuran (5.35 mL) at −78° C. with stirring. The mixture was stirred for 1.5 hrs at that temperature, poured to dry ice (33 g) slowly, and then tetrahydrofuran (2 mL) was added. The mixture was stirred at room temperature for 40 minutes, and water, toluene and tetrahydrofuran were added. The organic layer was separated, and extracted with a 1 mol/L aqueous solution of sodium hydroxide. These aqueous layers were combined, and was adjusted to pH 3 with an addition of concentrated hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (0.432 g).

Workup

  1. stirringThe mixture was stirred for 1.5 hrs at that temperature
  2. stirringThe mixture was stirred at room temperature for 40 minutes
  3. customThe organic layer was separated
  4. extractionextracted with a 1 mol/L aqueous solution of sodium hydroxide
  5. additionwas adjusted to pH 3 with an addition of concentrated hydrochloric acid
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8bb8ec007c01466d9a46b0552ab0358a
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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