Hydrochloric Acid → HCID 10898853, compound

To a solution of 3-ethoxycarbonylhexanedioic acid diethyl ester (10 g, 0.036 mol) in tert-butanol (100 mL) was added sodiumborohydride (6 g). The mixture was heated to reflux. Methanol (10 mL) was added in 3 aliquots over 30 minutes. The solution was heated at reflux for a further 30 minutes and allowed to cool. The solution was neutralised with 5 M hydrochloric acid with care. The solution was filtered and extracted with ethanol (2×50 mL). The solutions were combined and the solvent was removed at reduced pressure. The residue was extracted with ethanol (60 mL), filtered and concentrated at reduced pressure to yield the desired product as a clear, colourless liquid. This was analysed by NMR in D2O and found to be 3-hydroxymethylhexane-1,6-diol in a yield of 4.5 g (85%).

1. temperatureThe mixture was heated to reflux
2. temperatureThe solution was heated
3. temperatureat reflux for a further 30 minutes
4. temperatureto cool
5. filtrationThe solution was filtered
6. extractionextracted with ethanol (2×50 mL)
7. customthe solvent was removed at reduced pressure
8. extractionThe residue was extracted with ethanol (60 mL)
9. filtrationfiltered
10. concentrationconcentrated at reduced pressure

ORD record

ord-2059f4bcf0004ea4b51056bcbe0e15f0

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124806B2