Toluene → Methyl hexaethylene glycol chloroformate

HRID 895097

Reaction equation

HRID 895097 reaction equation
[CH3:1][O:2]CCOCCOCCOCCOCCOCCO.C(O)COCCOCCO.[C:31]([Cl:34])(Cl)=[O:32].C1(C)C=CC=CC=1.[CH2:42]([OH:60])[CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][OH:59]>CCOC(C)=O>[Cl:34][C:31]([OH:32])=[O:2].[CH3:1][CH:58]([OH:59])[CH2:57][O:56][CH2:55][CH2:54][O:53][CH2:52][CH2:51][O:50][CH2:49][CH2:48][O:47][CH2:46][CH2:45][O:44][CH2:43][CH2:42][OH:60]

Participants

7

Reactant 5

HCID 1140TolueneHCID 6371Phosgene2×HCID 8172Triethylene GlycolHCID 17472Hexaethylene GlycolHCID 902073,6,9,12,15,18-Hexaoxanonadecan-1-ol

Product 1

HCID 86587579Methyl hexaethylene glycol chloroformate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Monodispersed activated hexaethylene glycol monomethyl ether was prepared analogously to that of monodispersed triethylene glycol in Example 14 above. A 20% phosgene in toluene solution (35 mL, 6.66 g, 67.4 mmol phosgene) was chilled under a N2 atmosphere in an ice/salt water bath. Monodispersed hexaethylene glycol (1.85 mL, 2.0 g, 6.74 mmol) was dissolved in S mL anhydrous EtOAc and added to the phosgene solution via syringe. The reaction mixture was kept stirring in the ice bath for one hour, removed and stirred a further 2.5 hours at room temperature. The phosgene, EtOAc, and toluene were removed by vacuum distillation, leaving monodispersed methyl hexaethylene glycol chloroformate as a clear, oily residue.

Workup

  1. customremoved
  2. customThe phosgene, EtOAc, and toluene were removed by vacuum distillation

Sources & evidence

ORD record
ord-1de4de9c04eb4e6a8630a9804b4b229d
Source dataset
uspto-grants-2005_07
Patent number
US06913903B2

Linked notes

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