Water → 4'-(3-Ethoxy-1,1-dimethyl-3-oxopropyl)-2'-(3-methoxypropoxy)biphenyl-4-carboxylic acid

HRID 1690625Notes

Reaction equation

HRID 1690625 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:23])([CH3:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=2[O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:5][CH:4]=1)=[O:2].[Mn]([O-])(=O)(=O)=[O:31].[K+].O>CC(C)=O>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][C:15]([C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]([OH:31])=[O:2])=[CH:8][CH:7]=2)=[C:10]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:11]=1)([CH3:23])[CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 86633301Ethyl 3-[4'-formyl-2-(3-methoxypropoxy)biphenyl-4-yl]-3-methylbutanoate

Product 1

HCID 669063764'-(3-Ethoxy-1,1-dimethyl-3-oxopropyl)-2'-(3-methoxypropoxy)biphenyl-4-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 3-[4′-formyl-2-(3-methoxypropoxy)biphenyl-4-yl]-3-methylbutanoate (1.0 g, 2.5 mmol) was dissolved in acetone (40 mL) and a solution of potassium permanganate (1.4 g, 8.8 mmol) and water (20 mL) was added at room temperature. The mixture was stirred for 18 hrs and then filtered. Dichloromethane was added and the mixture was then acidified at 0° C. with HCl 1N. The aqueous layer was extracted three times with dichloromethane and the combined organic layers were washed twice with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 1.0 g, (96%) of the desired product as a brown solid.

Workup

  1. filtrationfiltered
  2. additionDichloromethane was added
  3. customwas then acidified at 0° C. with HCl 1N
  4. extractionThe aqueous layer was extracted three times with dichloromethane
  5. washthe combined organic layers were washed twice with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2149c4c965d64492bf1b45583c05e0cb
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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