2,2-Bis(bromomethyl)-1,3-propanediol → 5,5-Bis(bromomethyl)-2,2-dimethyl-1,3-dioxane

HRID 1669470

Reaction equation

HRID 1669470 reaction equation
[Br:1][CH2:2][C:3]([CH2:8][Br:9])([CH2:6][OH:7])[CH2:4][OH:5].[CH3:10][C:11]([CH3:13])=O.COC(OC)(C)C>>[Br:1][CH2:2][C:3]1([CH2:8][Br:9])[CH2:6][O:7][C:11]([CH3:13])([CH3:10])[O:5][CH2:4]1

Participants

3

Reactant 2

HCID 186922,2-Bis(bromomethyl)-1,3-propanediolHCID 23511411Acetone 2,2-dimethoxypropane

Product 1

HCID 145372285,5-Bis(bromomethyl)-2,2-dimethyl-1,3-dioxane

Procedure

TsOH monohydrate (0.1 eq) was added at 0° C. to a 0.2M solution of 2,2-bis(bromomethyl)propane-1,3-diol in acetone/2,2-dimethoxypropane (10:1) and the solution was stirred for 2 h at RT. Filtration over a pad of neutral alumina with EtOAc afforded the title compound as a white solid after evaporation of the solvent in vacuo (quant). 1H NMR (300 MHz, CDCl3, 300 K) 3.80 (s, 4H), 3.58 (s, 4H), 1.42 (s, 6H).

Workup

  1. filtrationFiltration over a pad of neutral alumina with EtOAc

Sources & evidence

ORD record
ord-206039df0661429e90e3c3ada0714444
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Linked notes

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