Hydrochloric Acid → Acrylic acid, 2-(hydroxymethyl)-, ethyl ester

Temperature

100 °C

Into a 2-liter separable flask fitted with a stirrer, a reflux condenser and a thermometer, dimethylsulfoxide (500 parts), water (170 parts), ethyl acrylate (200 parts), paraformaldehyde (purity: 80%, 72.5 parts) and diazabicyclo (2.2.2) octane (15.6 parts) were charged. They were heated to 100° C., and subjected to a reaction for 4 hours. Although the contents were not homogeneous at the time of the charging, they turned into a homogeneous clear mixture around 60° C. Dilute hydrochloric acid (500 parts) was then added, followed by extraction twice with diethylether (200 parts, each). The extract was dried over anhydrous magnesium sulfate. After the thus-dried extract was concentrated in an evaporator, the concentrate was subjected to distillation under reduced pressure. Ethyl 2-(hydroxymethyl)acrylate was obtained (yield: 193 parts). The reaction product was identified to be the target compound by IR and NMR, and its purity was determined to be 98.7% by GC.

1. customInto a 2-liter separable flask fitted with a stirrer, a reflux condenser
2. customsubjected to a reaction for 4 hours
3. customturned into a homogeneous clear mixture around 60° C
4. extractionfollowed by extraction twice with diethylether (200 parts
5. dry with materialThe extract was dried over anhydrous magnesium sulfate
6. extractionAfter the thus-dried extract
7. concentrationwas concentrated in an evaporator
8. distillationthe concentrate was subjected to distillation under reduced pressure

ORD record

ord-694f8600b5b34d06b51cdc9009263e7d

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985796B2