1-Bromo-3,4-(methylenedioxy)benzene → 8-(Benzo[d][1,3]dioxol-5-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1707245Notes

Reaction equation

HRID 1707245 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.Br[C:13]1[CH:18]=[CH:17][C:16]2[O:19][CH2:20][O:21][C:15]=2[CH:14]=1>C1COCC1>[O:19]1[C:16]2[CH:17]=[CH:18][C:13]([C:7]3([OH:10])[CH2:6][CH2:5][C:4]4([O:3][CH2:2][CH2:1][O:11]4)[CH2:9][CH2:8]3)=[CH:14][C:15]=2[O:21][CH2:20]1

Participants

4

Reactant 2

HCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 109128408-(Benzo[d][1,3]dioxol-5-yl)-1,4-dioxaspiro[4.5]decan-8-olYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,4-cyclohexanedione monoethylene ketal in dry THF was reacted with the Grignard reagent prepared from 4-bromo-1,2-methylenedioxybenzene as described in example 1 to give the product (52%, mp: 95°-96° C.). Calc'd for C15H18O5 : C, 64.74%; H, 6.52%. Found: C, 64.41%; H, 6.41%.

Sources & evidence

ORD record
ord-4c1ae5b631144b13be9ed77987ed31db
Source dataset
uspto-grants-1994_10
Patent number
US05352678

Reaction notes

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