[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:17])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][C:15]#[CH:16])[C:5](O)=[O:6].C(N1C=CN=C1)([N:20]1C=CN=C1)=O.[OH-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:17])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][C:15]#[CH:16])[C:5]([NH2:20])=[O:6]To a solution of 4.7 g 3,5-dimethyl-4-(3-ethynylpropoxy)benzoic acid in 100 ml dry tetrahydrofuran was added 3.7 g carbonyldiimidazole and the mixture was stirred 2 hrs. at room temperature. To the latter was added 10 ml concentrated ammonium hydroxide, and the mixture was stirred for 30 min., poured onto water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated to give 4.7 g 3,5-dimethyl-4-(3-ethynylpropoxy)benzamide, m.p. 81°-84° C.
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