Acetone → 2,2-Dimethyl-1,3-benzodioxole

HRID 731966Notes

Reaction equation

[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH3:9][C:10]([CH3:12])=O>>[CH3:9][C:10]1([CH3:12])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1

Participants

Reactant 2

HCID 180Acetone

HCID 289Catechol

Product 1

HCID 2858692,2-Dimethyl-1,3-benzodioxole

Procedure

As depicted in Scheme 3, catechol was cyclized with acetone under catalytic conditions, affording the corresponding 2,2-dimethylbenzo[d]1,3-dioxolane (C1). Intermediate (C1) was then treated with for example lead tetraacetate ubder acidic conditions, yielding the corresponding 2,2-dimethylbenzo[3,4-d]1,3-dioxolan-5-yl acetate (C2). Intermediate (C2) was then deprotected with strong base, providing a phenolic intermediate (C3), which was in turn reacted with intermediate (B5), as taught in scheme 2, affording a compound of formula I. Example 3 set forth below describes in detail the method by which compounds of formula I were prepared as shown in scheme 3.

Sources & evidence

ORD record: ord-0f68813b2ef34c9799719c75c6d4bd33
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585891B2

Reaction notes

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