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

HRID 1439880Notes

Reaction equation

HRID 1439880 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.[Mg].Br[C:14]1[CH:22]=[CH:21][C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1>C1COCC1>[O:18]1[C:17]2[CH:21]=[CH:22][C:14]([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:15][C:16]=2[O:20][CH2:19]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 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 1,4-cyclohexanedione monoethylene ketal (31.2 g, 0.2 mole) in 100 ml dry THF was added to a -60° C. solution of the Grignard reagent prepared from magnesium metal (7.2 g, 0.3 mole) and 5-bromo-1,3-benzodioxole (60.3 g, 0.3 mole). The mixture was allowed to warm to 25° C. and quenched with saturated NH4Cl and extracted with ether. The extracts were dried with Na2SO4 and the solvent removed in vacuo. The residue was crystallized from isopropyl ether to give the product (47.5 g, 85%, m.p: 103°-104° C.).

Workup

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ether
  3. dry with materialThe extracts were dried with Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-71b1f0e5a03448768274d776596a4bba
Source dataset
uspto-grants-1996_03
Patent number
US05496847

Reaction notes

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