Hydrochloric Acid → 2-(4-Chlorophenyl)-2-methylpropanal

HRID 1977704Notes

Reaction equation

HRID 1977704 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([CH3:20])([CH3:19])[C:17]#N)=[CH:14][CH:13]=1.[OH2:23].Cl>CCCCCC.C(OCC)C>[Cl:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([CH3:20])([CH3:19])[CH:17]=[O:23])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 101302194-Chloro-α,α-dimethylbenzeneacetonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 114353342-(4-Chlorophenyl)-2-methylpropanalYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

Diisobutylaluminum hydride (0.236 mol, 236 mL of a 1 M solution in hexane) is added over 90 minutes to a solution of p-chloro-α-methylhydratroponitrile (32.6 g, 0.181 mol) in diethyl ether under nitrogen at 0° C. After the addition is complete, water and 6 N hydrochloric acid are added to the reaction mixture while maintaining the temperature below 30° C. The resultant aqueous solution is stirred overnight at room temperature and extracted with diethyl ether. The organic extracts are combined, washed sequentially with 2 N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as an oil (31.1 g, 94% yield).

Workup

  1. additionAfter the addition
  2. temperaturewhile maintaining the temperature below 30° C
  3. extractionextracted with diethyl ether
  4. washwashed sequentially with 2 N hydrochloric acid and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff8c227e02404defa20bbddc4da75352
Source dataset
uspto-grants-2001_05
Patent number
US06235754B1

Reaction notes

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