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

HRID 2300043Notes

Reaction equation

HRID 2300043 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[CH:7]1([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH:16]=[O:17])[CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.N1C=CC=CC=1>[CH:7]1([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[C:16]([OH:2])=[O:17])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516875Potassium PermanganateHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehyde

Product 1

HCID 27793233-(Cyclopentyloxy)-4-methoxybenzoic acidYield 67%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

A solution of tetrabutylammonium bromide (111.68 g, 0.336 moles) in water (400 ml) was added under stirring to a solution of potassium permanganate (53.1 g, 0.336 moles) in water (1 l). The obtained solid was separated by filtration, washed with water and dissolved in 500 ml of pyridine. This solution was dropped into one of crude 3-cyclopentyloxy-4-methoxy benzaldehyde (obtained as described in J. Med. Chem., 1995, 38, page 4851) (74 g, 0.336 moles) in pyridine (200 ml), under stirring in water/ice. At the end 3 l of ice were added and it was acidified by dropping 850 ml of 12N HCl. The stirring was kept for further 1.5 hours, then the solid was separated by filtration and extracted under stirring for 30 minutes with ethyl acetate (2 l). The residual solid was removed and the mother liquors were further extracted with ethyl acetate (2×700 ml). The organic phases were washed with water, dried on sodium sulphate and concentrated to small volume to give 53.2 g of the title compound (yield: 67%).

Workup

  1. customThe obtained solid was separated by filtration
  2. washwashed with water
  3. dissolutiondissolved in 500 ml of pyridine
  4. customthe solid was separated by filtration
  5. extractionextracted
  6. customThe residual solid was removed
  7. extractionthe mother liquors were further extracted with ethyl acetate (2×700 ml)
  8. washThe organic phases were washed with water
  9. customdried on sodium sulphate
  10. concentrationconcentrated to small volume

Sources & evidence

ORD record
ord-39afcca033d64a7aa8c9b7295a1f7ea2
Source dataset
uspto-grants-2002_12
Patent number
US06498160B2

Reaction notes

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