Methylparaben → HCID 57770570, compound

To a stirred solution of methyl 4-hydroxybenzoate (30 g, 197 mmol, 1.0 mole equivalents), tetrahydro-4-pyranol (24 ml, 251 mmol, 1.3 mole equivalents) and triphenylphosphine (78 g, 297 mmol, 1.5 mole equivalents) in tetrahydrofuran (600 ml) at room temperature, was added diisopropyl azodicarboxylate (58 ml, 298 mmol, 1.5 mole equivalents) over a period of 15 minutes. The reaction mixture was stirred for 24 hours at room temperature. Another portion of diisopropyl azodicarboxylate (5 ml) and tetrahydro-4-pyranol (2 ml) was added and the reaction mixture was stirred for another 2 hours at room temperature. The reaction mixture was then quenched by the addition of a saturated aqueous solution of sodium hydrogen carbonate (500 ml) and ethyl acetate (500 ml). The organic phase was washed with water (2×250 ml), dried (magnesium sulfate), and was then concentrated in vacuo to give the crude product, methyl 4-(tetrahydro-2H-pyran-4-yloxy)benzoate, as a thick yellow oil (182 g).

1. stirringthe reaction mixture was stirred for another 2 hours at room temperature
2. customThe reaction mixture was then quenched by the addition of a saturated aqueous solution of sodium hydrogen carbonate (500 ml) and ethyl acetate (500 ml)
3. washThe organic phase was washed with water (2×250 ml)
4. dry with materialdried (magnesium sulfate)
5. concentrationwas then concentrated in vacuo

ORD record

ord-4c817bcd37ad497aa5f1196c3c1594c7

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288389B2