Chloroacetyl chloride → HCID 12500886, compound

HRID 237126Notes

Reaction equation

[Cl:1][CH2:2][C:3](Cl)=[O:4].CO[C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[O:10][CH3:11].C(N(CC)CC)C>CCCCCC>[Cl:1][C:2]1[C:3](=[O:4])[C:9]([O:10][CH3:11])([O:12][CH3:13])[C:8]=1[O:14][CH3:15]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 23.7 g (0.21 mole) of chloroacetyl chloride is added dropwise, in the course of 40 minutes, to a solution, cooled to 0°-5° C. and vigorously stirred, of 14.8 g (0.1 mole) of 1,1,2,2-tetramethoxyethylene and 23.2 g (0.23 mole) of triethylamine in 100 ml of absolute n-hexane. The greyish-brown suspension formed is stirred for 3 hours at 20° C.; the resulting salt is then filtered off with suction and washed with n-hexane, and the yellow filtrate is concentrated by evaporation. The intensive IR-absorption bands of the residue (30.4 g) confirm the formation of 2-chloro-3,3,4,4-tetramethoxy-1-chloroacetoxycyclobutene (5.71μ) and 2-chloro-3,4,4-trimethoxycyclobutenone (5.58; 6.1μ). According to the NMR spectrum, the reaction mixture contains 80±5% by weight of 2-chloro-3,3,4,4,-tetramethoxy-1-chloroacetoxybutene and 12±3% by weight of 2-chloro-3,4,4-trimethoxycyclobutenone, besides small amounts of unidentifiable by-products. By rapid separation by columnchromatography of 0.5 g of the crude residue, it is possible to obtain 0.1 g of pure 2-chloro-3,4,4-trimethoxycyclobutenone (eluant: hexane/diethyl ether in a volume ratio of 4:1).

Workup

temperaturecooled to 0°-5° C.
customThe greyish-brown suspension formed
filtrationthe resulting salt is then filtered off with suction
washwashed with n-hexane
concentrationthe yellow filtrate is concentrated by evaporation
customBy rapid separation by columnchromatography of 0.5 g of the crude residue, it

Sources & evidence

ORD record: ord-88a1f63055754d29a42c1c1a408e6686
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159387

Reaction notes

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