Hydrochloric Acid → 4-(Cyclopentyloxy)-3-methoxybenzoic acid

HRID 2230989Notes

Reaction equation

HRID 2230989 reaction equation
[CH:1]1([O:6][C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][C:8]=2[O:18][CH3:19])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C.O1CCOCC1>[CH:1]1([O:6][C:7]2[CH:17]=[CH:16][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[O:18][CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22724204Ethyl 4-cyclopentyloxy-3-methoxybenzoate

Product 1

HCID 227243044-(Cyclopentyloxy)-3-methoxybenzoic acidYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 4-cyclopentyloxy-3-methoxybenzoate (1.06 g) and 4N aqueous sodium hydroxide (4 ml) in ethanol (8 ml) and 1,4-dioxane (8 ml) was stirred at 80° C. for 3 hours. Then the mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic solution was washed with dilute hydrochloric acid and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 4-cyclopentyloxy-3-methoxybenzoic acid (730 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic solution was washed with dilute hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-bb7d17f58239468abf7ba1afaf02262b
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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