Dimethyl Carbonate → HCID 11268509, compound

HRID 2204017Notes

Reaction equation

HRID 2204017 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[C:6]1([PH+:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:25](=O)(OC)OC>>[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:25][P+:12]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 12021Dimethyl CarbonateHCID 11100188HCID 11100188, compound

Product 1

HCID 11268509HCID 11268509, compound

Procedure

In a reactor wherein air was replaced by N2, 300.0 g of (1.1 mol) triphenyl phosphine and 500 mL of methanol were added and cooled to 10° C. by a ice-bath. 250.8 g (1.1 mol) of fluoroboric acid aqueous solution (40 wt %) was then added dropwise under strong stirring. After one hour of reaction, the reaction temperature was increased to about 50° C., and the unreacted materials as well as the solvents, including water and methanol, were removed by distillation under vacuum to obtain triphenylphosphonium tetrafluoroborate. The phosphonium salt was then transferred to an autoclave, and 202.0 g (2.2 mol) of dimethyl carbonate was also introduced. After 6 hours of reaction at temperature of 160° C. and at pressure of from 1.4 MPa to 1.5 MPa, the crude product was obtained after distilling off the unreacted materials and solvent. 375.0 g of methyl triphenyl phosphonium tetrafluoroborate was obtained after washing and drying at 60° C. and 0.1 kPa for 4 hours.

Workup

  1. additionwas also introduced
  2. customAfter 6 hours of reaction at temperature of 160° C.
  3. customat pressure of from 1.4 MPa to 1.5 MPa, the crude product was obtained
  4. distillationafter distilling off the unreacted materials and solvent

Sources & evidence

ORD record
ord-78708aa9fcd24f09b52c0fc28b678bf0
Source dataset
uspto-grants-2016_06
Patent number
US09365596B2

Reaction notes

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