Sodium Hydroxide → HCID 54389871, compound

Methyl 2-hydroxy-4-octenoate (23)(7.04 g, 0.041 mol, 1.0 eq) is heated under reflux with a large excess of sodium hydroxide (13.5 g, 0.34 mol, 8.3 eq) in water (30 ml) and methanol (30 ml) for 1 hour. After cooling down to room temperature, the mixture is washed with hexane (50 ml) and the organic phase separated. The clear aqueous layer is acidified to pH 1 with concentrated hydrochloric acid and the resultant mixture is extracted with diethylether (3×50 ml), the combined organic layers being washed with brine (50 ml) thence dried over anhydrous magnesium sulphate and evaporated to give a colourless oil which slowly crystallised to furnish the product acid (21) as a white waxy solid, 5.72 g (88%), m p 37-38° C.

1. washthe mixture is washed with hexane (50 ml)
2. customthe organic phase separated
3. extractionthe resultant mixture is extracted with diethylether (3×50 ml)
4. washthe combined organic layers being washed with brine (50 ml)
5. dry with materialthence dried over anhydrous magnesium sulphate
6. customevaporated
7. customto give a colourless oil which
8. customslowly crystallised

ORD record

ord-b568d7a33e4a4ef0b6f225d27ff5108f

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05108751