Hydrochloric Acid → Methyl 2-chloro-4-methylbenzoate

HRID 2355270Notes

Reaction equation

HRID 2355270 reaction equation
Cl.O1CCOC[CH2:3]1.[Cl:8][C:9]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]>CO>[CH3:3][O:12][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:9]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 27357552-Chloro-4-methylbenzoic acid

Product 1

HCID 22019481Methyl 2-chloro-4-methylbenzoateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 4N hydrogen chloride in 1,4-dioxane (20 mL, 80 mmol) to 2-chloro-4-methylbenzoic acid (5.0 g, 29.3 mmol) in methanol (60 mL). Stir the reaction mixture at room temperature over the weekend. Concentrate the reaction mixture and partition the residue between ethyl acetate and saturated aqueous sodium bicarbonate solution. Separate the organic layer and extract the aqueous with ethyl acetate (2×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate to provide the title compound as a brownish oil (4.7 g, 25.5 mmol).

Workup

  1. concentrationConcentrate the reaction mixture
  2. custompartition the residue between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. customSeparate the organic layer
  4. extractionextract the aqueous with ethyl acetate (2×)
  5. washCombine the organic layers, wash with brine
  6. dry with materialdry over sodium sulfate
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-66e5bb73e8684828ab1f3a05f2a08438
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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