Carbon Dioxide → beta-(2'-Chloro-4-biphenylyl)propionaldehyde

HRID 1659068Notes

Reaction equation

HRID 1659068 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](Cl)=[O:17])=[CH:10][CH:9]=1.[OH-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].COCCOCCOC.C(=O)=O>C(COC)OC.CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH:16]=[O:17])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 8150DiglymeHCID 21526230beta-(2'-Chloro-4-biphenylyl)propionyl chlorideHCID 23715209Lithium tri-t-butoxyaluminum hydroxide

Product 1

HCID 21526069beta-(2'-Chloro-4-biphenylyl)propionaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

β-(2'-chloro-4-biphenylyl)propionyl chloride (28 g.) in 500 ml glyme is treated dropwise with a solution of lithium tri-t-butoxyaluminum hydroxide (25.5 g.) in 500 ml. diglyme while maintaining the reaction temperature at -70°C with dry ice. When addition is complete, the mixture is allowed to come to room temperature, is diluted with ether, and washed with water, dilute HCl and brine. The solvent is dried over sodium sulfate, evaporated under vacuo and the residue distilled to give β-(2'-chloro-4-biphenylyl)propionaldehyde

Workup

  1. additionWhen addition
  2. customto come to room temperature
  3. washwashed with water, dilute HCl and brine
  4. dry with materialThe solvent is dried over sodium sulfate
  5. customevaporated under vacuo
  6. distillationthe residue distilled

Sources & evidence

ORD record
ord-3ecf2911278d45a290a96d7446f64bee
Source dataset
uspto-grants-1976_06
Patent number
US03966801

Reaction notes

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