Water → HCID 21483907, compound

HRID 1415194Notes

Reaction equation

HRID 1415194 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:18]=[C:19]([O:22][CH3:23])[C:20]=1[Cl:21])[CH:11]=[CH:12][C:13](OCC)=[O:14].O.[OH-].[Na+]>CCOCC>[Cl:7][C:8]1[CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][OH:14])[CH:18]=[C:19]([O:22][CH3:23])[C:20]=1[Cl:21]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54466878HCID 54466878, compound

Product 1

HCID 21483907HCID 21483907, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (1.2 g., 0.032 mole) is suspended in dry ether (100 ml.) in a flask equipped with a stirrer, upright condenser and dropping funnel and protected from moisture. To this is added dropwise with stirring a solution of ethyl 3,4-dichloro-5-methoxycinnamate (4.3 g., 0.0156 mole) in dry ether (150 ml.) over a twenty 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 3-(3,4-dichloro-5-methoxyphenyl)propanol remains.

Workup

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

Sources & evidence

ORD record
ord-c108bf7ed8e14af3a1a66449615c1327
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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