Sodium Hydroxide → HCID 19091779, compound

HRID 488301Notes

Reaction equation

HRID 488301 reaction equation
C[O:2][C:3](=[O:34])[C:4](=[O:33])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:8]=[C:7]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:6]=1.[OH-].[Na+]>CO>[CH2:12]([O:11][C:9]1[CH:10]=[C:5]([C:4](=[O:33])[C:3]([OH:34])=[O:2])[CH:6]=[C:7]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:8]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53795776HCID 53795776, compound

Product 1

HCID 19091779HCID 19091779, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.7 g (5.7 mmol) of 3,5-bis(decyloxy)-alpha-oxobenzeneacetic acid methyl ester in 400 ml of hot methanol was added 6.2 ml (6.2 mmol) of 1.0N NaOH and the solution was stirred at reflux for 5 minutes. The solvent was removed at reduced pressure, water and 10 ml of 1N HCl were added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated to give 2.55 g (97% yield) of 3,5-bis(decyloxy)-alpha-oxobenzeneacetic acid as a waxy solid.

Workup

  1. temperatureat reflux for 5 minutes
  2. customThe solvent was removed at reduced pressure, water and 10 ml of 1N HCl
  3. additionwere added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-ebb41720c2ae43edbdc39845eee162bc
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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