Toluene → HCID 23509236, compound

HRID 1250001Notes

Reaction equation

HRID 1250001 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10]O.[C:12]([Cl:15])(Cl)=[O:13].C1(C)C=CC=CC=1.CC[O:25]CC>>[Cl:15][C:12]([O:13][CH2:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH3:10])=[O:25]

Participants

5

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 6371PhosgeneHCID 8178Triethylene glycol monomethyl ether

Product 1

HCID 23509236HCID 23509236, compoundYield 95%

Procedure

A solution of triethylene glycol monomethyl ether (2 g, 12.2 mmol) in ether (15 mL) was added dropwise to a stirred, ice-cold solution of 20% phosgene in toluene (11.36 mL, 21.92 mmol) over 20 min. The reaction mixture was allowed to warm to rt and stirring was continued for 15 h. Evaporation of the solvent give 2.63 g (95%) of the title compound. 1H NMR (CDCl3): δ4.44 (m, 2H), 3.37 (m, 2H), 3.68-3.63 (m, 6H), 3.55 (m, 2H), 3.38 (s, 3H).

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4ec7c00575744011957e2403c81fbdc6
Source dataset
uspto-grants-2002_01
Patent number
US06335429B1

Reaction notes

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