Water → 2-Benzyl-4-chlorobenzyl alcohol

HRID 1903614Notes

Reaction equation

HRID 1903614 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.O.[OH-].[Na+]>CCOCC>[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

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 130670812-Benzyl-4-chlorobenzoic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 155700662-Benzyl-4-chlorobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 28.4 g (0.75 mol) of lithium aluminum hydride in 800 ml of ether, which was cooled to 0° C., were added dropwise 85.1 g (0.345 mmol) 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 hours. The excess lithium aluminum hydride was discharged by the addition of 28.5 ml of water, 28.5 ml of 10% aqueous sodium hydroxide solution, and 85.5 ml of water. The precipitate was removed by filtration, and the filtrate was dried over sodium sulfate. Removal of the ether at reduced pressure gave a colorless oil which crystallized upon standing, mp 46.5°-49° C.

Workup

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

Sources & evidence

ORD record
ord-db4bbedefddf47e1a1019d4d025acd97
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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