Diethyl Ether → 4-Chloro-2-methylbenzaldehyde

HRID 857783Notes

Reaction equation

HRID 857783 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[C:4]([CH3:10])[CH:3]=1.CC(C[AlH]CC(C)C)C.CC[O:22]CC>C1COCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:22])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14487Diisobutylaluminum hydride2×HCID 1427424-Chloro-2-methylbenzonitrile

Product 1

HCID 27576584-Chloro-2-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred −78° C. solution of 4-chloro-2-methylbenzonitrile (5.00 g, 32.98 mmol) in Et2O (190 mL) was added 1 M DIBAL in THF (66.0 mL) over 10 min. After 5 h additional 1M DIBAL in THF (3.30 mL) was added dropwise and the solution was stirred for 1 hour. The reaction was quenched with water followed by concentrated H2SO4 and stirred at ambient temperature for 16 h. The solution was extracted into Et2O, dried (Na2SO4) and reduced in vacuo. 4-Chloro-2-methylbenzaldehyde was isolated as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 2.59 (s, 3H), 7.19 (s, 1H), 7.26 (d, J=8.2 Hz, 1H), 7.66 (d, J=8.2 Hz, 1H), 10.15 (s, 1H).

Workup

  1. customThe reaction was quenched with water
  2. stirringstirred at ambient temperature for 16 h
  3. extractionThe solution was extracted into Et2O
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-2e22399e618340f595a71f8e97a4e2f4
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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