Methyl iodide → 4-Butoxy-2-methylbenzoic acid

HRID 69405

Reaction equation

HRID 69405 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:15]N(C)CCN(C)C.C([Li])(CC)C.CI>C1COCC1.O>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH3:15])[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 729714-Butoxybenzoic acidHCID 178418400CID 53628100

Product 1

HCID 534398994-Butoxy-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-90 °C

Procedure

A mixture of 4-butoxybenzoic acid (10 g), N,N,N′,N′-tetramethylethylenediamine (13.2 g) and THF (75 mL) was cooled to −90° C., and sec-butyllithium (81 mL; 1.4 M in hexane) was added over the course of 30 minutes. After a further 30 minutes, the mixture was warmed to −78° C., and a solution of methyl iodide (12.8 mL) in THF (10 mL) was added dropwise. The reaction solution was allowed to warm to room temperature and the mixture was hydrolyzed with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel. The product with the molecular weight of 208.26 (C12H16O3) was obtained in this way; MS (ESI): 209 (M+H+).

Workup

  1. temperaturethe mixture was warmed to −78° C.
  2. temperatureto warm to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. customThe product with the molecular weight of 208.26 (C12H16O3) was obtained in this way

Sources & evidence

ORD record
ord-9dbf2c0103ca4e578abbdbf1db5703e5
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Linked notes

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