Water → HCID 57831644, compound

(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol (6, 1.17 g, 8.9 mmol) and 4-iodobenzylbromide (2.5 g, 8.4 mmol) were refluxed under Dean-Stark conditions in toluene (80 mL) in the presence of KOH (8.8 g, 154.0 mmol) for 12 h. The reaction mixture was allowed to cool down and H2O (30 mL) was added. After separation of the phases the water layer was washed with toluene (2×15 mL). Combined organic layers were washed with H2O (30 mL) and concentrated in vacuo. The residue was treated with 80% aq. AcOH (25 mL) for 48 h at rt. The solvent was removed in vacuo and the residue was co-evaporated twice with toluene/EtOH (30 mL, 5:1, v/v). The residue was dried under diminished pressure to afford (R)-3-(4-iodobenzyloxy)propane-1,2-diol (7, 100%, 2.3 g) as yellowish oil that was used in the next step without further purification.

1. temperatureto cool down
2. customAfter separation of the phases the water layer
3. washwas washed with toluene (2×15 mL)
4. washCombined organic layers were washed with H2O (30 mL)
5. concentrationconcentrated in vacuo
6. additionThe residue was treated with 80% aq. AcOH (25 mL) for 48 h at rt
7. customThe solvent was removed in vacuo
8. customThe residue was dried under diminished pressure

ORD record

ord-4a2b6cec95de48b898486aed8fba4cda

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102937B2