Oxalyl chloride → HCID 14501734, compound

A solution of oxalyl chloride (20 mL, 0.23 mol, 1.15 eq) in dry dichloromethane (50 mL) was added dropwise at room temperature, with stirring, to a solution of (2,2,2-trifluoroethoxy)ethanoic acid (int. Patent Appl., Publication No. WO 87/07270, 31.6 g, 0.2 mol) and N,N-dimethylformamide (5 drops) in dry dichloromethane (400 mL). The mixture was stirred for an additional hour, then heated under reflux for 2 hours, cooled and the bulk of the solvent removed by distillation (bp 40-45° C./760 mm Hg). The residue was transferred to a Claisen distillation flask and the remaining solvent and oxalyl chloride removed by distillation (bp 45-60° C./760 mm Hg). Vacuum distillation of the residue then afforded the product, bp 50-55°/25-32 mm Hg. δH (CDCl3) 4.00 (2H, q, 3JHF 8.3) and 4.57 (2H, s).

1. temperatureheated
2. temperatureunder reflux for 2 hours
3. temperaturecooled
4. customthe bulk of the solvent removed by distillation (bp 40-45° C./760 mm Hg)
5. distillationThe residue was transferred to a Claisen distillation flask
6. customthe remaining solvent and oxalyl chloride removed by distillation (bp 45-60° C./760 mm Hg)
7. distillationVacuum distillation of the residue
8. customthen afforded the product, bp 50-55°/25-32 mm Hg

ORD record

ord-5a974d909d5d4fd7b7820f92583938eb

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06166049