Cyclohexanol → 4-(Bromomethyl)cyclohexan-1-ol
Reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:8][CH2:9]C1(O)CCCCC1.COC1CCC(C(O)=O)CC1>>[Br:8][CH2:9][CH:4]1[CH2:5][CH2:6][CH:1]([OH:7])[CH2:2][CH2:3]1Participants
Procedure
Modified polyvinylbutryal containing a pendant group with cyclohexanol was prepared by the reaction of PVB with tetrahydropyranyl (THP) protected bromomethylcyclohexanol, followed by acid hydrolysis of the THP protection group. The THP-protected cyclohexanol-containing moiety was prepared by the following reaction sequence: 4-Methoxycyclohexanoic acid was reduced with borane-tetrahydrofuran complex to obtain 4-bromomethyl-cyclohexanol. This compound was treated with phosphorus tribromide to obtain the corresponding bromo compound. This bromo compound was reacted with trimethylsilyliodide to cleave the methoxy group to obtain 4-bromomethyl-cyclohexanol, which in turn was treated with dihyhdropyran to obtain the tetrahydropyranyl-protected bromomethylcyclohexanol. This preparation is represented by the following reaction scheme and further described in paragraphs a-d below. ##STR3## a) Preparation of 4-bromomethylcyclohexanol (C-3)
Workup
- customwas prepared by the reaction of PVB with tetrahydropyranyl (THP)
- customwas prepared by the following reaction sequence
Sources & evidence
- ORD record
- ord-78c9071ac414486f9393e4b9e93d513a
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750300
Reaction notes
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