Benzyl Alcohol → HCID 10878747, compound

HRID 1857063Notes

Reaction equation

[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Br-].[Na+].Cl[CH2:16][C@H:17]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]1.Cl>CN(C=O)C>[CH2:1]([O:8][CH2:16][C@H:17]1[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Benzyl alcohol (32.90 g, 0.155 mol) was dropped under ice cooling in a suspension of 60% sodium hydride (5.88 g, 0.155 mol) and DMF (150 ml). After emission of hydrogen gas, sodium bromide (9.67 g, 0.094 mol) was added thereto. A DMF solution (15 ml) of (R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane (11.747 g, 0.078 mol) prepared by the same manner as Example 3 was dropped in it. The temperature was raised to 120° C. and the mixture was stirred for 15 hours. After completion of the reaction the reaction mixture was cooled on ice bath and neutralized with 6% hydrochloric acid. The solution was extracted with ethyl acetate. The organic layer was washed with water and with saturated brine, dried over anhydrous sodium sulfate and condensed in vacuo. The crude product was distilled to give 9.627 g of (S)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane (yield 54%, b.p. 112° C. at 0.3 mmHg).

Workup

additionwas dropped in it
customAfter completion of the reaction the reaction mixture
temperaturewas cooled on ice bath
extractionThe solution was extracted with ethyl acetate
washThe organic layer was washed with water and with saturated brine
dry with materialdried over anhydrous sodium sulfate and condensed in vacuo
distillationThe crude product was distilled

Sources & evidence

ORD record: ord-3993a296d5f141c1baba9daa08f323f7
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143908

Reaction notes

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