1-Chloro-4-(2,2-diethoxyethoxy)benzene synthesis
- Product Name:1-Chloro-4-(2,2-diethoxyethoxy)benzene
- CAS Number:41964-04-9
- Molecular formula:C12H17ClO3
- Molecular Weight:244.71
Yield:41964-04-9 93%
Reaction Conditions:
with potassium hydroxide in N,N-dimethyl acetamide at 20;Heating;
Steps:
Preparation of 2-aryloxyacetaldehyde diethyl acetals 1a-1t
General procedure: A 250 mL round-bottomed flask was charged with phenol 3 (50 mmol), DMAC (100 mL) and KOH(6.6 g, 100 mmol), followed by adding dropwise with 2-bromoacetaldehyde diethyl acetal (15.1 g, 75mmol) at room temperature. After the addition, the mixture was stirred under refluxing for 2-3 hoursuntil the reaction was completed based on GC determination. Then the mixture was cool to roomtemperature and extracted with ether (100 mL x 3). The combined organic layers were subsequentlywashed with 5% NaOH aqueous solution and water, dried over anhydrous MgSO4, filtered off andremoved solvent to dryness in vacuo. The residual was finally purified by flash columnchromatography on SiO2 (petroleum ether/ethyl acetate) to afford the desired 2-aryloxyacetaldehydediethyl acetals.
References:
Sun, Nan;Huang, Peng;Wang, Yifan;Mo, Weimin;Hu, Baoxiang;Shen, Zhenlu;Hu, Xinquan [Tetrahedron,2015,vol. 71,# 29,p. 4835 - 4841] Location in patent:supporting information
