Water → HCID 22420297, compound

HRID 1032412Notes

Reaction equation

HRID 1032412 reaction equation
C[O:2][C:3]([CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[OH:2][CH2:3][CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14838442HCID 14838442, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22420297HCID 22420297, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

At room temperature and while stirring, a solution of 16.91 g (82 mmol) of 2-methoxycarbonylmethylchroman in 150 ml of absolute tetrahydrofuran is added dropwise within a period of 30 minutes to a suspension of 3.11 g (82 mmol) of lithium aluminium hydride in 150 ml of absolute diethyl ether. Stirring is continued for a further 16 hours at room temperature and then the whole is carefully decomposed with 3.1 ml of water, 3.1 ml of sodium hydroxide solution (15% strength) and 9.3 ml of water. The precipitate formed is filtered off with suction and the filtrate is concentrated by evaporation in vacuo. The oily residue is dissolved in diethyl ether. The ethereal solution is washed with water, dried over sodium sulphate and concentrated by evaporation in vacuo. 14.36 g (98.3%) of 2-(2-hydroxyethyl)chroman are obtained in the form of a colourless oil.

Workup

  1. stirringStirring
  2. customThe precipitate formed
  3. filtrationis filtered off with suction
  4. concentrationthe filtrate is concentrated by evaporation in vacuo
  5. dissolutionThe oily residue is dissolved in diethyl ether
  6. washThe ethereal solution is washed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-873caa0c83334e3ba05d790a7102c1cb
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

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