Methyl-3,5-didecoxybenzoate → Benzoic acid, 3,5-bis(decyloxy)-

HRID 1757773Notes

Reaction equation

HRID 1757773 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:7]=[C:6]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:5]=1>CO.[OH-].[Na+]>[CH2:22]([O:21][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:7]=1)[C:3]([OH:32])=[O:2])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 1

HCID 10343663Methyl-3,5-didecoxybenzoate

Product 1

HCID 10320747Benzoic acid, 3,5-bis(decyloxy)-Yield 96.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 6.0 g (0.013 mol) of 3,5-bis(decyloxy)benzoic acid methyl ester in 300 ml of methanol and 40 ml of 1N sodium hydroxide was stirred at reflux for 3.5 hours. The reaction mixture was concentrated under reduced pressure and the residue was acidified with 6N HCl. The product was extracted with ethyl acetate and the dried extract was concentrated under reduced pressure to a yellow solid. Recrystallization from methanol-water gave 5.45 g (94% yield, mp 56°-58°) of 3,5-bis(decyloxy)benzoic acid.

Workup

  1. temperatureat reflux for 3.5 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionThe product was extracted with ethyl acetate
  4. extractionthe dried extract
  5. concentrationwas concentrated under reduced pressure to a yellow solid
  6. customRecrystallization from methanol-water

Sources & evidence

ORD record
ord-8510f08b129b4e5380a144f7ec0969c3
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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