Water → 2-Hydroxymethyl-8-methoxy-chroman

HRID 1939276Notes

Reaction equation

HRID 1939276 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 in the course of 1 h, with stirring, at 20° C. to a suspension of 9.5 g (0.25 mol) of lithium aluminium hydride in 525 ml of anhydrous diethyl ether. The batch 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 successively added dropwise, with cooling. The organic phase is decanted off and evaporated. The residue is recrystallised twice from dichloromethane/petroleum ether.

Workup

  1. temperaturewith cooling
  2. customThe organic phase is decanted off
  3. customevaporated
  4. customThe residue is recrystallised twice from dichloromethane/petroleum ether

Sources & evidence

ORD record
ord-a4049886c32341f6a393d9b3c22fbb78
Source dataset
uspto-grants-1997_12
Patent number
US05696137

Reaction notes

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