Sulfuric Acid → Methyl 1-(4-chlorophenyl)cyclobutane-1-carboxylate

HRID 28775Notes

Reaction equation

HRID 28775 reaction equation
C[CH:2]1[CH2:5][CH2:4][C:3]1([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:6]([OH:8])=[O:7].S(=O)(=O)(O)O.[C:21](=O)([O-])[O-].[Na+].[Na+]>CO>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:3]2([C:6]([O:8][CH3:21])=[O:7])[CH2:4][CH2:5][CH2:2]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 664325861-(4-Chlorophenyl)-2-methylcyclobutane-1-carboxylic acid

Product 1

HCID 67363367Methyl 1-(4-chlorophenyl)cyclobutane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-(4-chlorophenyl)cyclobutanecarboxylic acid (5.0 g, 23.73 mmol) in anhydrous methanol was added 1 mL of the concentration of sulfuric acid. The mixture was refluxed for overnight. The mixture was neutralized to pH 4-5 with sodium carbonate. The solvent was evaporated. The residue was dissolved in ethyl acetate (50 mL), washed with brine (3×10 mL), dried over MgSO4. The crude product was used for the next reaction without further purification.

Workup

  1. temperatureThe mixture was refluxed for overnight
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  4. washwashed with brine (3×10 mL)
  5. dry with materialdried over MgSO4
  6. customThe crude product was used for the next reaction without further purification

Sources & evidence

ORD record
ord-a8e24215a21e4033b1e0210b40818937
Source dataset
uspto-grants-2008_09
Patent number
US07419999B2

Reaction notes

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