2-Propenoic acid, (4-methoxyphenyl)methyl ester synthesis
- Product Name:2-Propenoic acid, (4-methoxyphenyl)methyl ester
- CAS Number:133208-88-5
- Molecular formula:C11H12O3
- Molecular Weight:192.21
Yield:133208-88-5 92%
Reaction Conditions:
Stage #1: acrylic acidwith potassium carbonate in N,N-dimethyl-formamide at 0; for 1 h;
Stage #2: p-methoxybenzyl chloride in N,N-dimethyl-formamide at 100; for 12 h;
Steps:
2. General procedure for preparation of acrylate 2
General procedure: Benzyl acrylate (2a), methyl acrylate (2k), ethyl acrylate (2l), butyl acrylate (2m), isobutyl acrylate (2n), and tert-butyl acrylate (2o) were obtained from TCI or Aldrich, and were used as supplied. The other acrylates were synthesized by a modification of the reported procedure as follows.2 A 100 mL round-bottom flask equipped with a stirring bar was charged with K2CO3 (1660 mg, 12.0 mmol) and DMF (20 mL). To the solution, acrylic acid (820 μL, 12.0 mmol) was added at 0 °C and the reaction was allowed to stir at 0 °C for 1 h. To the mixture, corresponding alkyl halide (10.0 mmol) was added and the mixture was stirred at the indicated temperature. To the reaction mixture, brine was added, and the mixture was extracted with CH2Cl2 (3 * 25 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The remaining residue was purified by silica gel column chromatography (hexane/ethyl acetate) to afford the desired acrylate 2.
References:
Odanaka, Yuki;Kanemitsu, Takuya;Iwasaki, Kanako;Mochizuki, Yukiko;Miyazaki, Michiko;Nagata, Kazuhiro;Kato, Masaru;Itoh, Takashi [Tetrahedron,2019,vol. 75,# 2,p. 209 - 219] Location in patent:supporting information
