Water → 2-Hydroxymethyl-8-methoxy-chroman

HRID 1728322Notes

Reaction equation

HRID 1728322 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13](OCC)=[O:14])[CH2:9][CH2:8]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)C>[OH:14][CH2:13][CH:10]1[CH2:9][CH2:8][C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[O:11]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18787171Ethyl 8-methoxy-chroman-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 234318182-Hydroxymethyl-8-methoxy-chroman

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

59.0 g (0.25 mol) of ethyl 8-methoxy-chroman-2-carboxylate in 525 ml of anhydrous tetrahydrofuran are added dropwise to a suspension of 9.5 g (0.25 mol) of lithium aluminium hydride in 525 ml of anhydrous diethyl ether at 20° C. in the course of 1 hour, while stirring. The mixture is stirred overnight, and 9.5 ml of water, 9.5 ml of 15% strength sodium hydroxide solution and 28.4 ml of water are then added dropwise in succession, while cooling. The organic phase is decanted and evaporated. The residue is recrystallised twice from methylene chloride/petroleum ether.

Workup

  1. stirringThe mixture is stirred overnight
  2. temperaturewhile cooling
  3. customThe organic phase is decanted
  4. customevaporated
  5. customThe residue is recrystallised twice from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-b32a360a7e074eb192b6ab0a14ec39a5
Source dataset
uspto-grants-1994_07
Patent number
US05326771

Reaction notes

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