Sodium Iodide → HCID 22145405, compound

HRID 1825367Notes

Reaction equation

HRID 1825367 reaction equation
[C:1](=[O:13])([O:5][C:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[O:2][CH2:3]Cl.N1C(C)=CC=CC=1C.[I-:22].[Na+]>CC(C)=O.CCCCCC>[C:1](=[O:13])([O:5][C:6]1([CH3:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[O:2][CH2:3][I:22]

Participants

6

Reactant 3

HCID 5238Sodium Iodide2×HCID 79372,6-LutidineHCID 22145386Chloromethyl 1-methylcyclohexyl carbonate

Product 1

HCID 22145405HCID 22145405, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

Chloromethyl 1-methylcyclohexyl carbonate (2.07 g) in acetone (7.5 ml) was treated with 2,6-lutidine (0.116 ml). Sodium iodide (2.25 g) was then added and the mixture was stirred for 1.5 h. More sodium iodide (1.5 g) was then added and stirring was continued. After a total of 2.5 h the acetone was removed and CH2Cl2/water were added and the layers separated. The dichloromethane layer was washed with 5% aqueous Na2S2O3, dried (MgSO4) and evaporated to leave an oil. This was taken up in hexane (50 ml) and loaded onto a silica gel column, and the column was eluted with 5% ethyl acetate in hexane to give iodomethyl 1-methylcyclohexyl carbonate containing some of the starting chloromethyl compound, δ(CDCl3) 1.26-1.35 (2H, m), 1.40-1.65 (9H, m, including s at δ 1.52), 2.10-2.20 (2H, m), 5.69 (s) and 5.91 (s) (together 2H, ratio 1:5) ppm.

Workup

  1. stirringstirring
  2. customAfter a total of 2.5 h the acetone was removed
  3. additionCH2Cl2/water were added
  4. customthe layers separated
  5. washThe dichloromethane layer was washed with 5% aqueous Na2S2O3
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto leave an oil
  9. washthe column was eluted with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-630637044ae146a3b4d6ddbde99e1a2b
Source dataset
uspto-grants-2006_05
Patent number
US07045619B2

Reaction notes

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