Water → HCID 21483918, compound

HRID 1415192Notes

Reaction equation

HRID 1415192 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH2:17][C:18](OCC)=[O:19])[CH:11]=[C:12]([O:15][CH3:16])[C:13]=1[Cl:14].O.[OH-].[Na+]>CCOCC>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:17][CH2:18][OH:19])[CH:11]=[C:12]([O:15][CH3:16])[C:13]=1[Cl:14]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21483908HCID 21483908, compound

Product 1

HCID 21483918HCID 21483918, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (1.2 g., 0.032 moles) is suspended in dry ether (100 ml.) in a flask equipped with a stirrer, dropping funnel and protected from moisture. To this is added dropwise with stirring a solution of ethyl 3,4-dichloro-5-methoxyphenylacetate (4.1 g., 0.0156 mole) in dry ether (150 ml.) over a 20-minute period. The mixture is stirred for an additional 30 minutes. Then, with vigorous stirring 1.2 g. of water is added carefully followed by 15% sodium hydroxide (1.5 ml.) and an additional 4.5 ml. of water. The ether solution is filtered from the granular inorganic salts which then are washed with additional ether. The combined ether solutions are washed with water and dried (Na2SO4). Upon evaporation of the ether, 2-(3,4-dichoro-5-methoxyphenyl)ethanol remains.

Workup

  1. customequipped with a stirrer
  2. additionTo this is added dropwise
  3. stirringThen, with vigorous stirring 1.2 g
  4. filtrationThe ether solution is filtered from the granular inorganic salts which
  5. washthen are washed with additional ether
  6. washThe combined ether solutions are washed with water
  7. dry with materialdried (Na2SO4)
  8. customUpon evaporation of the ether, 2-(3,4-dichoro-5-methoxyphenyl)ethanol

Sources & evidence

ORD record
ord-7ab806e7ea3a4ba0be7cf9d572cffceb
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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