Water → HCID 22000907, compound

HRID 1976302Notes

Reaction equation

HRID 1976302 reaction equation
[CH3:1][C:2]1([CH2:15][C:16](OCC)=[O:17])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:14])[C:6]([CH3:13])=[CH:7][C:8]=2[CH3:12])[O:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][C:2]1([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:14])[C:6]([CH3:13])=[CH:7][C:8]=2[CH3:12])[O:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54108263HCID 54108263, compound

Product 1

HCID 22000907HCID 22000907, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of ethyl (2,5,7,8-tetramethylchroman-2-yl)acetate (8.00 g) in tetrahydrofuran (THF) (16 ml) was added dropwise to the suspension of lithium aluminum hydride (1.10 g) in THF (40 ml) under reflux. After refluxing for 2 hours, a solution of water (1 ml) in THF (5 ml) was added to the reaction mixture. The insoluble material was filtered off and the filtrate was concentrated under reduced pressure to give a residue. The residue was purified by chromatography over silica gel (AcOEt-hexane 10:90) to give 2-(2,5,7,8-tetramethylchroman-2-yl)ethanol as a solid (5.00 g).

Workup

  1. temperatureunder reflux
  2. temperatureAfter refluxing for 2 hours
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give a residue
  6. customThe residue was purified by chromatography over silica gel (AcOEt-hexane 10:90)

Sources & evidence

ORD record
ord-955ebaca38514ed7865cbe45d76538f3
Source dataset
uspto-grants-2001_05
Patent number
US06225480B1

Reaction notes

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