Ethyl Acetate → 1-(5-chloro-2-methoxyphenyl)ethan-1-ol

HRID 2359280Notes

Reaction equation

HRID 2359280 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:8]([OH:10])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2404341-(5-Chloro-2-methoxyphenyl)ethanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 580463561-(5-chloro-2-methoxyphenyl)ethan-1-olYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-(5-chloro-2-methoxyphenyl)ethanone (7.97 g, 43.1 mmol) in anhydrous tetrahydrofuran (40 mL) at 0° C. was added a 1M solution of lithium aluminium hydride In THF (14.2 mL, 14.2 mmol). After 3 hours, ethyl acetate (200 mL) was added and the mixture was washed with a 1M aqueous solution of hydrogen chloride (50 mL). The organic phase was concentrated in vacuo to afford the title compound (6.97 g, 86%)

Workup

  1. washthe mixture was washed with a 1M aqueous solution of hydrogen chloride (50 mL)
  2. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-7505c43781744a0eb7946276fa70cf8c
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

Loading…