1-Chlorooctane → Methyl octyl carbonate

HRID 542575Notes

Reaction equation

HRID 542575 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:10](=[O:15])([O:13][CH3:14])[O:11][CH3:12]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[C:10](=[O:13])([O:15][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[O:11][CH3:12].[C:10](=[O:15])([O:13][CH2:14][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[O:11][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 2

HCID 81421-ChlorooctaneHCID 12021Dimethyl Carbonate

Product 2

HCID 6421218Methyl octyl carbonateYield 74%HCID 9904000Dicaprylyl CarbonateYield 5%

Reagents, catalysts & solvents 2

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 6228DimethylformamideSolvent

Procedure

1-Chlorooctane (37.17 g, 0.25 mole), dimethyl carbonate (90.0 g, 1.0 mole), tetra-n-butylphosphonium bromide (3.39 g, 0.01 mole) and N,N-dimethylformamide (200 ml) are heated to 115° C. for 24 hours. After work-up as described for Example 34, distillation gives 34.8 g (74 percent yield based on 1-chlorooctane) of methyl 1-octyl carbonate, b.p. 113° C.-114° C. (17 torr) and 1.9 g (5 percent yield based on n-octyl chloride) of di-1-octyl carbonate, b.p. 129° C.-130° C. (0.5 torr).

Workup

  1. distillationAfter work-up as described for Example 34, distillation

Sources & evidence

ORD record
ord-65277641874141db8de3b78f3580abd0
Source dataset
uspto-grants-1987_04
Patent number
US04658041

Reaction notes

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