Hydrochloric Acid → 5-Chloro-2-[(cyclopentyloxy)methyl]benzoic acid

HRID 660228Notes

Reaction equation

HRID 660228 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[CH:14]1([OH:19])[CH2:18][CH2:17][CH2:16][CH2:15]1.CC(C)([O-])C.[K+].Cl>O1CCCC1>[Cl:13][C:10]1[CH:11]=[CH:12][C:3]([CH2:2][O:19][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:4]([CH:9]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7298CyclopentanolHCID 23665647Potassium tert-butoxideHCID 51358462Methyl 2-(bromomethyl)-5-chlorobenzoate

Product 1

HCID 688635365-Chloro-2-[(cyclopentyloxy)methyl]benzoic acidYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(bromomethyl)-5-chlorobenzoate (200 mg, 0.80 mmol), cyclopentanol (379 mg 4.4 mmol), and potassium tert-butoxide (448 mg, 4.0 mmol) in tetrahydrofuran (8 mL) was stirred at room temperature for 3 hours. The mixture was acidified with 2 N hydrochloric acid and the acidic aqueous mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1/1) to afford 100 mg (49%) of the title compound:

Workup

  1. extractionthe acidic aqueous mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-6dbe416882df46068945a0089e32e20d
Source dataset
uspto-grants-2011_12
Patent number
US08084476B2

Reaction notes

Loading…