Tetrahydrofuran → 2-Chloro-6-methylbenzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#N.CC(C[AlH]CC(C)C)C.C1C[O:23]CC1>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH:4]=[O:23]Participants
4
Procedure
To a stirred solution of 2-chloro-6-methylbenzonitrile (1 g, 6.6 mmol) in THF (15 mL) under argon at 0° C. a solution of DIBAL (1 M in THF, 7 mL, 7 mmol) was added dropwise over 5 minutes. After 3 hr at 0° C., the reaction mixture was brought to room temperature and further stirred overnight. The reaction mixture was quenched with 5% sulfuric acid at 0° C., extracted with ether, washed with brine and dried (MgSO4). Concentration provided 2-chloro-6-methylbenzaldehyde (0.92 g) which was used without further purification.
Workup
- waitthe reaction mixture was brought to room temperature and further stirred overnight
- customThe reaction mixture was quenched with 5% sulfuric acid at 0° C.
- extractionextracted with ether
- washwashed with brine
- dry with materialdried (MgSO4)
- concentrationConcentration
Sources & evidence
- ORD record
- ord-00e6caf674b84519b051ef1effd61f56
- Source dataset
- uspto-grants-2003_01
- Patent number
- US06506747B1
Reaction notes
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