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

HRID 1858934Notes

Reaction equation

HRID 1858934 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:21]=[CH:20][C:16]2[O:17][CH2:18][O:19][C:15]=2[CH:14]=1.[Mg]>C1COCC1>[O:17]1[C:16]2[CH:20]=[CH:21][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:19][CH2:18]1

Participants

5

Reactant 3

HCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 5462224Magnesium

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 (25 g, 160 mmole) in dry THF (250 ml) was reacted with the Grignard reagent prepared from 5-bromo-1,3-benzodioxole (40 g, 200 mmole) and magnesium (4.8 g, 200 mmole) as described in example 3 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-75ef34da9b4743908017da52f71a727d
Source dataset
uspto-grants-2000_11
Patent number
US06153611

Reaction notes

Loading…