Toluene → HCID 23509236, compound

HRID 916519Notes

Reaction equation

HRID 916519 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): δ 4.44 (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-3656354f3cf8422086b388440d4f33c3
Source dataset
uspto-grants-2007_09
Patent number
US07270801B2

Reaction notes

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