Methyl iodide → 4-chloro-2-ethylBenzoic acid

HRID 2398570Notes

Reaction equation

HRID 2398570 reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.[Cl:8][C:9]1[CH:17]=C[C:12]([C:13]([OH:15])=[O:14])=[C:11](C)[CH:10]=1.CI>O1CCCC1.C([Li])CCC.CCCCCC>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[C:7]([CH2:5][CH3:6])[CH:17]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 3482694-Chloro-2-methylbenzoic acid

Product 1

HCID 105594154-chloro-2-ethylBenzoic acid

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 178418339ButyllithiumSolvent

Procedure

The starting material is prepared as follows: To the ice-cooled, stirred solution of 9.6 ml of diisopropylamine in 200 ml of tetrahydrofuran, 42 ml of 1.6 molar butyl lithium in hexane are slowly added, followed by the solution of 5.1 g of 4-chloro-2-methylbenzoic acid in 60 ml of tetrahydrofuran. The mixture is stirred for 15 minutes at 0°, then cooled to -70° and 7.5 ml of methyl iodide are slowly added. It is allowed to warm to 0°, quenched with water, the aqueous layer separated and acidified with concentrated hydrochloric acid. It is extracted with methylene chloride, the extract dried and evaporated, to yield the 4-chloro-2-ethylbenzoic acid.

Workup

  1. customThe starting material is prepared
  2. additionare slowly added
  3. temperaturecooled to -70°
  4. temperatureto warm to 0°
  5. customquenched with water
  6. customthe aqueous layer separated
  7. extractionIt is extracted with methylene chloride
  8. customthe extract dried
  9. customevaporated

Sources & evidence

ORD record
ord-ad76b28e52a5414b9faa164f273b0525
Source dataset
uspto-grants-1977_05
Patent number
US04025505

Reaction notes

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