Sodium Hydroxide → HCID 21182373, compound

HRID 1872370Notes

Reaction equation

HRID 1872370 reaction equation
[CH3:1][C:2]1[C:3]2[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:13]=[CH:12][C:4]=2[O:5][C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[C:3]2[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:13]=[CH:12][C:4]=2[O:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21182385HCID 21182385, compound

Product 1

HCID 21182373HCID 21182373, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Ethyl 3-methyl-5-octylbenzo[b]furan-2-carboxylate (1.44 g) in ethanol (20 ml) was added 10% NaOH aqueous solution (2.2 ml), and stirred for 2 hours at ambient temperature, and evaporated under reduced pressure. The residue was adjusted to pH 3.0 with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 3-Methyl-5-octylbenzo[b]furan-2-carboxylic acid (1.00 g).

Workup

  1. customevaporated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e798980838a148419cc852bf21300165
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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