Water → HCID 19001664, compound

HRID 486946Notes

Reaction equation

HRID 486946 reaction equation
[CH:1]([C:4]1[C:5]([CH2:13][C:14](O)=[O:15])=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH:1]([C:4]1[C:5]([CH2:13][CH2:14][OH:15])=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19001695HCID 19001695, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19001664HCID 19001664, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6.25 g of (6-isopropyl-1,3-benzodioxol-5-yl)acetic acid (crude crystal) in 30 ml of tetrahydrofuran was dropwise added to a suspension of 1.6 g of lithium aluminum hydride in 40 ml of tetrahydrofuran under cooling with ice. The obtained mixture was stirred overnight. 1.6 ml of water, 1.6 ml of a 15% aqueous solution of sodium hydroxide and 4.8 ml of water were added to the resulting mixture successively under cooling with ice. The obtained mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain 4.51 g of the title compound as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. filtrationThe obtained mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5b603488a68c4bd280da61287d0e5098
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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