Methanol → HCID 178501285, compound

Temperature

60 °C

A 250-mL round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was charged with 4-hydroxycyclohexane-1-carboxylic acid (15.7 g, 108.90 mmol, 1.00 equiv) in methanol (90 mL). Sulfuric acid (0.8 mL) was added to the mixture slowly. The resulting solution was stirred for 10 hr at 60° C. The reaction was then quenched by the addition of 200 mL of sodium bicarbonate (sat.). The resulting solution was extracted with 3×200 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting trans-methyl 4-hydroxycyclohexane-1-carboxylate (16.6 g, 96%) was obtained as a light yellow oil.

1. customA 250-mL round-bottom flask, purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customThe reaction was then quenched by the addition of 200 mL of sodium bicarbonate (sat.)
4. extractionThe resulting solution was extracted with 3×200 mL of ethyl acetate
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-165ee679b3bb49bebe64baa402bdf67b

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212190B2