Water → 2-(Hydroxymethyl)chroman

HRID 1032409Notes

Reaction equation

HRID 1032409 reaction equation
C[O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[OH:2][CH2:3][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14838439Methyl 3,4-dihydro-2H-1-benzopyran-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 27948162-(Hydroxymethyl)chromanYield 99.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

At room temperature and while stirring, a solution of 36.4 g (0.19 mol) of 2-methoxycarbonylchroman in 400 ml of absolute tetrahydrofuran is added dropwise within a period of 1 hour to a suspension of 7.2 g (0.19 mol) of lithium aluminum hydride in 400 ml of absolute diethyl ether. After continuing to stir for a further 16 hours at room temperature, the reaction mixture is carefully decomposed with 7.2 ml of water, 7.2 ml of sodium hydroxide solution (15% strength) and 21.6 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. 31 g (99.3%) of 2-hydroxymethylchroman are thus obtained in the form of a colourless oil.

Workup

  1. stirringto stir for a further 16 hours at room temperature
  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-94039e6159fd4e728c69861fb7230fe0
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

Loading…