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Dehydration of alcohols

7 real reactions from the literature, on secondary alcohols, allylic alcohols, tertiary alcohols and halohydrins. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Dehydration of alcohol: 1-vinylcyclohexyl alcohol (an allylic alcohol) with TsOH; Hexane gives vinylcyclohexene (the cyclic conjugated diene). 81% yield.

    Dehydration of alcoholPCT Int. Appl. WO2008007109
  2. Dehydration of alcohol: a secondary alcohol with MsCl / Et3N; CH2Cl2 gives the six-membered cycloalkene.

    Dehydration of alcoholOrg. Lett. 2015, 17, 2570
  3. Dehydration of alcohol: a tertiary alcohol with 1) TsOH / Me2CO; 2) Na2CO3 / H2O; workup gives 3,4,5,6,7,8-hexahydro-1(2H)-naphthalenone (the tetrasubstituted six-membered cycloalkene). 90% yield.

    Dehydration of alcoholSynlett 1999, 1033
  4. Dehydration of alcohol: 2-bromo-1-indanol (a halohydrin) with TsOH; PhMe gives 2-bromo-1H-indene (the trisubstituted five-membered cycloalkene).

    Dehydration of alcoholOrganometallics 2000, 19, 5464
  5. Dehydration of alcohol: cyclohexanol (a secondary alcohol) with H2SO4, Δ gives cyclohexene (the six-membered cycloalkene).

    Dehydration of alcoholOrg. Synth. Coll. Vol. 1, p. 183
  6. Dehydration of alcohol: 2-pentanol (a secondary alcohol) with H2SO4; Δ gives trans-2-pentene (the trans-1,2-disubstituted alkene).

    Dehydration of alcoholOrg. Synth. Coll. Vol. 1, p. 430
  7. Dehydration of alcohol: 3-chloro-alpha-methylbenzenemethanol (a benzylic alcohol) with KHSO4; Δ gives m-chlorostyrene (the terminal alkene).

    Dehydration of alcoholOrg. Synth. Coll. Vol. 3, p. 204