Benzyl Bromide → Furan, tetrahydro-3-(phenylmethoxy)-

HRID 1065951Notes

Reaction equation

HRID 1065951 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)C1C=CC=CC=1.[OH:17][CH:18]1[CH2:22][CH2:21][O:20][CH2:19]1.[H-].[Na+]>O1CCOCC1>[O:20]1[CH2:21][CH2:22][CH:18]([O:17][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:19]1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 7503Benzyl ChlorideHCID 99603-Furanol, tetrahydro-HCID 24758Sodium hydride

Product 1

HCID 11240801Furan, tetrahydro-3-(phenylmethoxy)-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Thus, benzylchloride or benzylbromide can be reacted at elevated temperature with the alkololate from 3-hydroxytetrahydrofurane and sodium hydride, suspended in dioxane to yield the (3-tetrahydrofuryl)-benzylether which is an active herbicide against grassy weeds (German Offenlegungsschrift No. 2724675).

Sources & evidence

ORD record
ord-c3ed228d32a342318500e97ec64e40db
Source dataset
uspto-grants-1982_05
Patent number
US04331821

Reaction notes

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