Chloromethyl Methyl Ether → HCID 67340619, compound

4-Hydroxymethyl-benzonitrile (3.1 g, 23.3 mmoles) was combined with N,N-diisopropylethylamine (4.9 mL, 28 mmoles) in 100 mL of anhydrous THF. To this solution was added MOMCl (3.5 mL, 46.1 mmoles) and the mixture was stirred at room temperature for 16 hours. After this period a solution of NH4OH/H2O (1:1, 20 mL) was added (-MOMCl) and the solution was stirred for 15 minutes. After this period the reaction mixture was evaporated in vacuo (-THF) and the resulting mixture was extracted with DCM (3×30 mL). The combined DCM layer was dried over anhydrous Na2SO4, evaporated in vacuo, and the resulting crude product was purified using flash silica chromatography (0-20% EtOAc/Hexane) to yield 1.6 g (39% yield) of 4-Methoxymethoxymethylbenzonitrile as a colorless liquid.

1. stirringthe solution was stirred for 15 minutes
2. customAfter this period the reaction mixture was evaporated in vacuo (-THF)
3. extractionthe resulting mixture was extracted with DCM (3×30 mL)
4. dry with materialThe combined DCM layer was dried over anhydrous Na2SO4
5. customevaporated in vacuo
6. customthe resulting crude product was purified

ORD record

ord-0ae113a68d3742ca94c6097f2018f25a

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07998986B2