Cyclohexanone → (2-Chlorocyclohex-1-enyl)-methanol

HRID 1861869Notes

Reaction equation

HRID 1861869 reaction equation
C1(=O)CCCCC1.[CH2:8]1[CH2:13][C:12]([CH:14]=[O:15])=[C:11]([Cl:16])[CH2:10][CH2:9]1.[BH4-].[Na+].[Cl-].[Ce+3].[Cl-].[Cl-]>>[Cl:16][C:11]1[CH2:10][CH2:9][CH2:8][CH2:13][C:12]=1[CH2:14][OH:15]

Participants

4

Reactant 3

HCID 7967CyclohexanoneHCID 118048922-Chlorocyclohex-1-enecarbaldehydeHCID 131723797Sodium borohydride cerium chloride

Product 1

HCID 12611392(2-Chlorocyclohex-1-enyl)-methanolYield 46%

Procedure

Commercially available cyclohexanone was converted to (2-chlorocyclohex-1-enyl)carboxaldehyde according to General Procedure E. Sodium borohydride/cerium chloride reduction of the above carboxaldehyde, in accordance with the method described in General Procedure C gave the intermediate (2-chlorocyclohex-1-enyl)-methanol in 46% yield, which was characterized: 1H NMR (CDCl3, 300 MHz) δ=1.61-1.75 (m, 4H), 2.15 (br s, 1H), 2.22-2.27 (m, 2H), 2.33-2.37 (m, 2H), 4.24 (br s, 2H). The title compound was obtained from (2-chloro-cyclohex-1-enyl)methanol according to General Procedure C. Spectroscopic data: 1H NMR (D6 DMSO, 300 MHz) δ=1.52-1.69 (m, 4H), 2.07-2.11 (m, 2H), 2.28-2.35 (m, 2H), 3.48 (br s, 4H), 4.22 (br s, 2H), 4.76 (s, 1H), 7.41 (s, 1H), 7.54 (s, 1H).

Sources & evidence

ORD record
ord-ab014c5d57604eb5acb3d45ac92d983e
Source dataset
uspto-grants-2003_03
Patent number
US06534542B2

Reaction notes

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