Benzyl Bromide → 2-(Hydroxymethyl)-3-(phenylmethoxy)-4H-pyran-4-one

HRID 1249786

Reaction equation

HRID 1249786 reaction equation
[OH:1][CH2:2][C:3]1[O:4][CH:5]=[CH:6][C:7](=[O:10])[C:8]=1[OH:9].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[OH:1][CH2:2][C:3]1[O:4][CH:5]=[CH:6][C:7](=[O:10])[C:8]=1[O:9][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 98696223-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

Product 1

HCID 217925452-(Hydroxymethyl)-3-(phenylmethoxy)-4H-pyran-4-one

Procedure

The title compound was prepared by the method outlined for 2-hydroxymethyl-3-benzyloxy-6-methyl-pyran-4(1B)-one, using 7.1 g (50 mmol, 1 eq.) of 2-hydroxymethyl-3-hydroxy-pyran-4(1 H)-one and 9.5 g benzyl bromide (55 mmol, 1.1 eq.) to yield the crude product as an organe oil. Further purification by column chromatography on silica gel (eluant: 10% CH3OH/90% CHCl3) furnished the pure product (9.4 g, 81%) as a bright yellow oil. (Looker and Clifton (1986).

Workup

  1. customto yield the crude product as an organe oil

Sources & evidence

ORD record
ord-271da8747afa47808b6e219f5988638b
Source dataset
uspto-grants-2002_01
Patent number
US06335353B1

Linked notes

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