Benzene → 8-Methylidene-1,4-dioxaspiro[4.5]decane

HRID 418478Notes

Reaction equation

HRID 418478 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH:12]1C=CC=CC=1.C(OCC)C>O>[CH2:12]=[C:8]1[CH2:9][CH2:10][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 3283Diethyl EtherHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 109537438-Methylidene-1,4-dioxaspiro[4.5]decaneYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,4-Dioxaspiro[4.5]decan-8-one (21 g, 0.13 mol) in dry benzene (50 mL, 0.6 mol) was added to ethylenetriphenylphosphorane [prepared from dimsyl sodium and methyltriphenylphosphonium bromide (106 g, 0.291 mol) in dimethyl sulfoxide (600 mL, 8 mol)] The mixture was stirred at room temperature overnight and poured into a separating funnel containing ethyl ether (500 mL) and water (500 mL). The organic layer was separated and the aqueous phase was extracted with ethyl ether (2×500 mL). The combined ether layers were washed with water (500 mL) and brine (500 mL), and dried. The solvents were removed under reduced pressure and the residue was purified by flash chromatography to afford the desired product (18.0 g, 85%).

Workup

  1. additionpoured into a separating funnel
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with ethyl ether (2×500 mL)
  4. washThe combined ether layers were washed with water (500 mL) and brine (500 mL)
  5. customdried
  6. customThe solvents were removed under reduced pressure
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4bbca5c465504b91bda52d9e624154eb
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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