Acetone → HCID 11149825, compound

HRID 2224664Notes

Reaction equation

HRID 2224664 reaction equation
[CH2:1]([OH:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:10][C:11]([CH3:13])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:10][C:11]1([CH3:13])[O:9][CH2:1][C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5146Salicyl AlcoholHCID 6101p-Toluenesulfonic acid

Product 1

HCID 11149825HCID 11149825, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

First the hydroxyl groups of Salicyl alcohol were protected with acetone in refluxing benzene with the catalysis of para-toluenesulfonic acid to give 2,2-Dimethyl-4H-benzo[1,3]dioxine in quantitive yield. Friedel-craft acylation of this compound with AlCl3 and acetyl chloride in refluxing chloroform afforded 1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-ethanone in good yield. This was further brominated in chloroform with the catalysis of benzoyl peroxide to give 2-bromo-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)-ethanone, which was reduced to the chiral or nonchiral bromohydrine with borane and borane/oxazaborolidine, respectively. The title epoxide was generated by the addition of the above bromohydrine to a suspension of NaH in THF, as described previously.

Sources & evidence

ORD record
ord-55a23335ef454a7ebca5343bcea3e4ef
Source dataset
uspto-grants-2008_05
Patent number
US07378438B2

Reaction notes

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