Pyridine → Capryloyloxyethyl acrylate

A solution of 2-hydroxyethyl caprylate (HEC) (1 mol; 188.3 g) in pyridine (1.25 mol; 98.9 g; 100.7 ml) was added under continuous stirring at 5°-10° C. into a solution of freshly distilled acryloyl chloride (1.12 mol; 101.4 g) in benzene (300 ml). The mixture was further stirred for 2 hours at the reaction temperature, extracted with 800 ml of 2% hydrochloric acid, the emulsion formed was broken by addition of ether and the aqueous layer was repeatedly extracted with ether until the reaction on capryloyloxyethyl acrylate was negative. The combined ether extracts were washed with water, solution of potassium hydrogencarbonate (KHCO3), and water and dried with magnesium sulfate (MgSO4). Ether was removed by distillation under normal pressure and the product was distilled after addition of octylpyrocatechol as an inhibitor. The overall yield of raw product was 74.9%. The obtained fractions contained 60 to 93% of capryloyloxyethyl acrylate. The product with purity 99.8% was obtained by redistillation; b.p. 111° C./66.7 Pa. Elemental analysis for C13H22O4 theory: 64.44% C, 9.15% H; found 64.23% C; 9.41% H. The infrared and 13C-NMR spectra proved the expected structure.

1. extractionextracted with 800 ml of 2% hydrochloric acid
2. customthe emulsion formed
3. extractionthe aqueous layer was repeatedly extracted with ether until the reaction on capryloyloxyethyl acrylate
4. washThe combined ether extracts were washed with water, solution of potassium hydrogencarbonate (KHCO3), and water
5. dry with materialdried with magnesium sulfate (MgSO4)
6. customEther was removed by distillation under normal pressure
7. distillationthe product was distilled
8. additionafter addition of octylpyrocatechol as an inhibitor
9. customThe product with purity 99.8% was obtained by redistillation

ORDレコード

ord-1c5fac6161984213ab5abff5cfdeb26e

出典データセット

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04950733