Sodium Sulfate → 2-(3-bromo-4-methoxyphenyl)ethanol

HRID 1662754Notes

Reaction equation

HRID 1662754 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([Br:20])[CH:13]=1)C.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Br:20][C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][OH:9])[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 57419861Ethyl 3-bromo-4-methoxyphenylacetate

Product 1

HCID 230022542-(3-bromo-4-methoxyphenyl)ethanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 10.7 g of LAH in THF (600 ml) was added dropwise a solution of 70.0 g of ethyl(3-bromo-4-methoxyphenyl)acetate in THF (200 ml) at an internal temperature of −12 to −3° C. After stirring at an internal of 0° C. or lower for one hour, Na2SO4/10 hydrate was added slowly. After foaming ended, filtration was carried out. The filtrate was concentrated under reduced pressure to obtain 45.0 g of the title compound (light yellow oil).

Workup

  1. filtrationfiltration
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e500808f0c544d0c9585c10d367da5a9
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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