Chloroacetic Acid → 2-(Tert-butoxy)acetic acid

A suspension of sodium t-butoxide (24.1 g) in t-butanol (150 ml) was cooled in a water bath and treated drop-wise with a solution of chloroacetic acid (11.4 g) in t-butanol (30 ml). The mixture was heated under reflux for 5 h then concentrated in vacuo. The resultant white solid was dried in vacuo for 16 h then water (10 ml) was added and the mixture was filtered. The filtrate was treated with diethyl ether (150 ml), then cooled in an ice bath, stirred and acidified to pH1 with 2N sulphuric acid. The layers were separated and the aqueous layer was further extracted with diethyl ether. The combined organic extracts were dried MgSO4) and concentrated in vacuo to afford Intermediate 32 (11.1 g). 1H NMR (400 MHz, CDCl3, δ ppm) 1.27 (9H, s), 4.04 (2H, s).

1. temperaturewas cooled in a water bath
2. temperatureThe mixture was heated
3. temperatureunder reflux for 5 h
4. concentrationthen concentrated in vacuo
5. customThe resultant white solid was dried in vacuo for 16 h
6. additionwater (10 ml) was added
7. filtrationthe mixture was filtered
8. additionThe filtrate was treated with diethyl ether (150 ml)
9. temperaturecooled in an ice bath
10. customThe layers were separated
11. extractionthe aqueous layer was further extracted with diethyl ether
12. concentrationconcentrated in vacuo

ORD record

ord-dede1551c2954d3c941b8431e84fbd93

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07528148B2