Dimethylformamide → 6-Methoxy-2-naphthaldehyde
Reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.CN(C)[CH:16]=[O:17]>>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([CH:16]=[O:17])[CH:11]=[CH:10]2Participants
Procedure
Another embodiment of this invention comprises preparing 2-bromo-6-methoxynaphthalene as described herein, converting the 2-bromo-6-methoxynaphthalene into a Grignard reagent, and reacting the Grignard reagent with N,N-dimethylformamide (DMF) which yields after workup, 6-methoxy-2-naphthaldehyde. The Grignard reagent is formed by adding finely divided magnesium and, optionally a crystal of iodine, to a solution of 2-bromo-6-methoxynaphthalene in a suitable ether, such as diethyl ether or tetrahydrofuran in a dry, inert environment, and stirring the mixture at a temperature in the range of about 25° to about 80° C. The reaction of the resultant Grignard reagent with DMF is preferably conducted by adding the DMF portionwise to the Grignard reagent while stirring the mixture at a temperature in the range of about 25° to about 100° C., followed by acid hydrolysis. The following Example 57 is based in part on the procedure of A. Horeau, J. Jacques and R. Emiliozzi, Bull. Soc. Chim. Fr. 1959, at page 1857.
Sources & evidence
- ORD record
- ord-f8b17007fa19484383896e4434eb776c
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05756851
Reaction notes
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