Sodium Hydroxide → 3,5-Bis(3-methoxypropyl)benzoic acid

HRID 658250

Reaction equation

HRID 658250 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH:15]=1)[C:9]([O:11]C)=[O:10].[OH-].[Na+]>C1COCC1.CO.CCOC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH:15]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57456871Methyl 3,5-bis(3-methoxypropyl)benzoate

Product 1

HCID 574568723,5-Bis(3-methoxypropyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 3,5-bis(3-methoxypropyl)benzoate (1 eq.) from the previous step in THF/MeOH (2:1 v/v, 0.1 M) was added 2 M aqueous NaOH (2 eq.). After stirring at rt for 72 h, the reaction was diluted with EtOAc. The organic extract was washed with 10% aqueous HCl solution, brine, dried over MgSO4, and concentrated in vacuo to afford the title compound as an oil.

Workup

  1. extractionThe organic extract
  2. washwas washed with 10% aqueous HCl solution, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60904fa2d34b4224aaab9150b6badf8e
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Linked notes

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