Hydrochloric Acid → Methyl 1-phenylcyclopentane-1-carboxylate

HRID 1729064Notes

Reaction equation

HRID 1729064 reaction equation
[C:1]1([C:7]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:16]O>>[CH3:16][O:13][C:12]([C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 661671-Phenylcyclopentanecarboxylic acid

Product 1

HCID 11790325Methyl 1-phenylcyclopentane-1-carboxylateYield 88%

Procedure

A solution of 1-phenyl-1-cyclopentanecarboxylic acid (2.00 g, 10.51 mmol) in 30 mL methanol saturated with HCl was stirred at reflux for two hours. The reaction mixture was allowed to cool and the solvent was evaporated. The residue was dissolved in 50 mL dichloromethane and washed with 2N sodium hydroxide (3×25 mL). The organic layer was washed with water (2×25 mL) and dried (Na2SO4). Evaporation of the solvent gave 1.89 g (88%) of methyl-1-phenyl-1-cyclopentanecarboxylate as a pale yellow liquid and was used in the next step without further purification. CIMS 205 m/z (M+1).

Workup

  1. temperatureat reflux for two hours
  2. temperatureto cool
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in 50 mL dichloromethane
  5. washwashed with 2N sodium hydroxide (3×25 mL)
  6. washThe organic layer was washed with water (2×25 mL)
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6d1a841b5d7b4f7eaa65adf2e7fc492c
Source dataset
uspto-grants-1994_07
Patent number
US05331010

Reaction notes

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