Sodium Hydroxide → 2-Benzyl-4-chlorobenzyl alcohol

HRID 2296266Notes

Reaction equation

HRID 2296266 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li].[H-].[OH-].[Na+]>CCOCC.O>[CH2:7]([C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[CH2:16][OH:17])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 3028194LithiumHCID 130670812-Benzyl-4-chlorobenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 155700662-Benzyl-4-chlorobenzyl alcohol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 28.4 g (0.75 mole) of lithium aluminum hydride in 800 ml of ether, which was cooled to 0°, was added dropwise 85.1 g (0.345 mmole) of 2-benzyl-4-chlorobenzoic acid in 250 ml of ether. The mixture was allowed to warm to room temperature, and was stirred for 2 hr. The excess lithium alluminum hydride was discharged by the addition of 28.5 ml of water, 28.5 ml of 10% aqueous sodium hydroxide, and 85.5 ml of water. The precipitate was removed by filtration and the filtrate was dried with sodium sulfate. Removal of the ether at reduced pressure gave a colorless oil which crystallized upon standing, mp 46.5°-49°.

Workup

  1. customThe precipitate was removed by filtration
  2. dry with materialthe filtrate was dried with sodium sulfate
  3. customRemoval of the ether at reduced pressure
  4. customgave a colorless oil which
  5. customcrystallized

Sources & evidence

ORD record
ord-f189c3c297354cfdbc2900572b2adbec
Source dataset
uspto-grants-1984_01
Patent number
US04428878

Reaction notes

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