Phosphoric Acid → 3,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonitrile

反応式

C(OC1C(C)=CC(O)=C(C)C=1C)(=O)C.CC(O)(C#N)C=C.P(=O)(O)(O)O.B(F)(F)F.C([O:34][C:35]1[C:36]([CH3:50])=[C:37]2[C:42](=[C:43]([CH3:46])[C:44]=1[CH3:45])[O:41][C:40]([CH3:49])([C:47]#[N:48])[CH2:39][CH2:38]2)(=O)C>>[OH:34][C:35]1[C:36]([CH3:50])=[C:37]2[C:42](=[C:43]([CH3:46])[C:44]=1[CH3:45])[O:41][C:40]([CH3:49])([C:47]#[N:48])[CH2:39][CH2:38]2

参加物

反応物 5

HCID 1004Phosphoric Acid

HCID 6356Boron trifluoride

HCID 1190244-Hydroxy-2,3,6-trimethylphenyl acetate

HCID 144156756-Acetoxy-2,5,7,8-tetramethyl-2-cyanochromane

HCID 23317073Methylvinyl ketone cyanohydrin

生成物 1

HCID 116802373,4-Dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-carbonitrile収率 15%

実験手順

Using the method described in Example 1, last paragraph, 25.0 g (0.129 mole) of 4-acetoxy-2,3,5-trimethylphenol were reacted with 12.3 g (0.129 mole) of methyl vinyl ketone cyanohydrin, stabilized with phosphoric acid, and with 13.3 g (0.129 mole) of BF3. Conventional working up of the reaction mixture gave, according to analysis by gas chromatography, 25% of 6-acetoxy-2,5,7,8-tetramethyl-2-cyanochromane; colorless crystals, melting point 149°-151° C. In addition, 15% of 6-hydroxy-2,5,7,8-tetramethyl-2-cyanochromane were obtained.

後処理

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出典と根拠

ORDレコード: ord-1dc89288a4c74d72b98ee03e5df95ad9
出典データセット: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04268446

反応ノート

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