Hydrochloric Acid → HCID 54168322, compound

HRID 1782752Notes

Reaction equation

HRID 1782752 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](OC)=[O:28])=[CH:21][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO.Cl>O1CCCC1>[O:7]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:21][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21226445Aluminium lithium hydride2×HCID 53953054HCID 53953054, compound

Product 1

HCID 54168322HCID 54168322, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

20.1 ml of a 1 molar solution of lithium aluminium hydride in tetrahydrofuran is introduced. While stirring, a solution of 12.0 g of methyl 3-[4-(4-phenoxybutoxy)-phenyl]propanoate in 40 ml of THF is added dropwise in such a way that the mixture just starts to boil. The mixture is stirred at room temperature for 30 minutes. 1 ml of methanol is cautiously added to the suspension in order to hydrolyze excess lithium aluminium hydride. The mixture is then added to 1 molar hydrochloric acid and extracted with ethyl acetate. The organic phase is separated off, washed with saturated sodium chloride solution and dried over anhydrous sodium sulphate. Filtration and evaporation result in 10.9 g of product.

Workup

  1. stirringThe mixture is stirred at room temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is separated off
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-4af938b5bcb34c07b5af84808ffa2d71
Source dataset
uspto-grants-2009_03
Patent number
US07498460B2

Reaction notes

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