Hydrochloric Acid → 1-(4-Chlorophenyl)cyclobutanecarbaldehyde

HRID 1650931Notes

Reaction equation

HRID 1650931 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([C:22]#N)[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.Cl.CC[O:27]CC>CCCCCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([CH:22]=[O:27])[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 99423881-(4-Chlorophenyl)cyclobutanecarbaldehyde

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A 1M solution of diisobutylaluminium hydride in hexane (100 ml) was added dropwise to a stirred solution of 1-(4-chlorophenyl)cyclobutanecarbonitrile (19.1 g) in dry ether (50 ml) at -30° C. under nitrogen. The mixture was allowed to warm to 0° C. and was kept at that temperature for 30 minutes. The mixture was cooled to -30° C. and 5N hydrochloric acid (100 ml) was added dropwise with stirring. The mixture was filtered to separate a solid and the filtrate was extracted with ether. The solid was added to the ether extracts which were washed with water and dried. Removal of the solvent gave 1-(4-chlorophenyl)cyclobutanecarbaldehyde as a yellow oil.

Workup

  1. temperatureThe mixture was cooled to -30° C.
  2. filtrationThe mixture was filtered
  3. customto separate a solid
  4. extractionthe filtrate was extracted with ether
  5. additionThe solid was added to the ether extracts which
  6. washwere washed with water
  7. customdried
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-2810d27f0e2549d3bfd218053aaef743
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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