Acetic Acid → 2-[(1,1-Dimethylethyl)oxy]-6-chlorobenzaldehyde

HRID 374959Notes

Reaction equation

HRID 374959 reaction equation
[CH3:1][C:2]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:7]=1[C:8]#N)([CH3:4])[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.C(O)(=[O:27])C>C1(C)C=CC=CC=1>[CH3:1][C:2]([O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:7]=1[CH:8]=[O:27])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 189963822-[(1,1-Dimethylethyl)oxy]-6-chlorobenzonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 189963802-[(1,1-Dimethylethyl)oxy]-6-chlorobenzaldehydeYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-[(1,1-dimethylethyl)oxy]-6-chlorobenzonitrile (9.22 g, 44.0 mmol) in toluene (100 mL) cooled in an ice-bath was added diisobutylaluminum hydride (1M in hexane, 48.4 mL, 48.4 mmol) keeping the temperature less than 10° C. The reaction was stirred for 1 h and was poured into a mixture of 10% aqueous acetic acid (100 mL) and ice. The mixture was filtered through Celite, the layers separated and the aqueous layer extracted with ether (2 times). The combined organic layers were washed with saturated sodium bicarbonate, brine, dried (MgSO4) and concentrated to afford 9.07 g (97%) of 2-[(1,1-dimethylethyl)oxy]-6-chlorobenzaldehyde as a yellow oil.

Workup

  1. customthe temperature less than 10° C
  2. filtrationThe mixture was filtered through Celite
  3. customthe layers separated
  4. extractionthe aqueous layer extracted with ether (2 times)
  5. washThe combined organic layers were washed with saturated sodium bicarbonate, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf09d9f0fbe642269707d4f68b28844b
Source dataset
uspto-grants-1996_01
Patent number
US05482974

Reaction notes

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