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35.1.4.1.2 Method 2: Reaction with Hypochlorous Acid

DOI: 10.1055/sos-SD-035-00187

Pfeiffer, W. D.Science of Synthesis, (200735174.

The reaction of hypochlorous acid with 1-methylcyclohex-1-ene (7) in dichloromethane affords 1-chloro-2-methylenecyclohexane (8) and 6-chloro-1-methylcyclohex-1-ene (9) in 60% combined yield and 25% of 2-chloro-1-methylcyclohexan-1-ol (10) (Scheme 4).[‌13‌] Similarly, citral (11, X=CHO), methyl geranate (11, X=CO2Me), geraniol (11, X=CH2OH), and geranyl acetate (11, X=CH2OAc) react to give the corresponding allylic chlorides 12 in 6080% isolated yields. α-Ionone (13) gives a mixture of the allylic chlorides 14 and 15 with hypochlorous acid.[‌14‌] 2-(Chloromethyl)-4,4-dimethylpent-1-ene is obtained from 2,4,4-trimethylpent-1-ene in 46% yield.[‌15‌]

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