Water → HCID 86672568, compound

HRID 1918354Notes

Reaction equation

HRID 1918354 reaction equation
C1(C)C=CC=C(CC[O:9][C:10](=[O:29])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[C:13]([CH:27]=[O:28])[CH:12]=2)C=1.[Li+].[OH-].O>C1COCC1>[CH:27]([C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[O:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=1)[C:10]([OH:29])=[O:9])=[O:28]

Participants

5

Reactant 3

HCID 962Water2×HCID 3939Lithium Hydroxide2×HCID 86672569HCID 86672569, compound

Product 1

HCID 86672568HCID 86672568, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.0 g of 3-Formyl-4-(2-m-tolyl-ethoxy)-benzoic acid 2-m-tolyl-ethyl ester and 1.7 g of LiOH (Monohydrate) were stirred in 30 ml of THF and 2 ml of water at room temperature for 16 h. Then, an additional 1 g of LiOH (monohydrate) was added and the mixture stirred at room temperature for 4 h. Then, 100 ml of water were added, the THF evaporated and the aqueous layer was washed twice with diisopropylether, 100 ml each. The aqueous layer was then acidified to pH=3 using aqueous HCl-solution and the crude product collected by filtration. Chromatography on silica gel using a gradient EA/HEP to EA yielded 1.2 g of the title compound that was used without further purification.

Workup

  1. customthe THF evaporated
  2. washthe aqueous layer was washed twice with diisopropylether, 100 ml each
  3. filtrationthe crude product collected by filtration

Sources & evidence

ORD record
ord-71929d64ae16465ba89e556aabb8e271
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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