Lithium Hydroxide → Oxane-4-carboxylic acid

Methyl tetrahydro-2H-pyran-4-carboxylate (270 g, 1.87 mol) was diluted in ethanol (2 L). A 1M aqueous LiOH solution (1870 ml, 1.87 mol) was added (slight exotherm) at RT and the reaction was stirred for 3 hrs. The reaction mixture was concentrated to ca. 1 L and acidified to pH 2 with 5M HCl solution. The aqueous solution was extracted with ethyl acetate (3×600 ml) and the organic layer was dried (MgSO4) and evaporated to dryness to give a white solid (230.3 g, 94%).

1. concentrationThe reaction mixture was concentrated to ca. 1 L
2. extractionThe aqueous solution was extracted with ethyl acetate (3×600 ml)
3. dry with materialthe organic layer was dried (MgSO4)
4. customevaporated to dryness

ORD record

ord-76e9fb2770784b0a8abd2575d9391bec

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728035B2