Pyridine → Chloromethyl 1-methylcyclohexyl carbonate

HRID 1825366Notes

Reaction equation

HRID 1825366 reaction equation
[CH3:1][C:2]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.N1C=CC=CC=1.Cl[C:16]([O:18][CH2:19][Cl:20])=[O:17]>ClCCl>[C:16](=[O:17])([O:8][C:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[O:18][CH2:19][Cl:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 115501-MethylcyclohexanolHCID 62754Chloromethyl chloroformate

Product 1

HCID 22145386Chloromethyl 1-methylcyclohexyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1-Methylcyclohexanol (4.57 g) in dichloromethane (40 ml) was cooled in an ice-bath and treated with pyridine (3.24 ml). Chloromethyl chloroformate (3.65 ml) in dichloromethane (10 ml) was added dropwise through a pressure-equalising funnel. The mixture was stirred for 2 h and then washed with water (2×), dried (MgSO4) and then evaporated to leave a reddish-coloured oil, which was dissolved in dichloromethane and filtered through silica gel (230-400 mesh ASTM) to give (after evaporation) chloromethyl 1-methylcyclohexyl carbonate as a colourless oil (8.97 g), υmax(CH2Cl2) 2940, 2865, 1763, 1444, 1346, 1292, and 1237 cm−1; δ(CDCl3) 1.25-1.70 (11H, m), 2.12-2.18 (2H, m), 5.69 (2H,s) ppm.

Workup

  1. washwashed with water (2×)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto leave a reddish-coloured oil, which
  5. filtrationfiltered through silica gel (230-400 mesh ASTM)

Sources & evidence

ORD record
ord-2a2d5a7978ee4de487846b862515fab4
Source dataset
uspto-grants-2006_05
Patent number
US07045619B2

Reaction notes

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