Iodine → 1-(4-(1,3-Dioxolan-2-yl)phenyl)cyclohexanol

HRID 1884268Notes

Reaction equation

HRID 1884268 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[O:15][CH2:14][CH2:13][O:12]2)=[CH:7][CH:6]=1.[C:16]1(=[O:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C1COCC1>[O:12]1[CH2:13][CH2:14][O:15][CH:11]1[C:8]1[CH:9]=[CH:10][C:5]([C:16]2([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 7967CyclohexanoneHCID 27738422-(4-Bromophenyl)-1,3-dioxolane2×HCID 5462224Magnesium

Product 1

HCID 154477571-(4-(1,3-Dioxolan-2-yl)phenyl)cyclohexanolYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Magnesium turnings (14.6 g, 600 mmol) was placed in a dry 4-necked flask. Dry THF (50 mL) and a crystal of iodine were added. A mixture of 2-(4-bromophenyl)-[1,3]-dioxolane (Tetrahedron, 57, No.28, (2001), 5991-6002) (135 g, 589 mmol) in dry THF (200 mL) was slowly added to initiate the reaction. After the reaction had started, the addition of 2-(4-bromophenyl)-[1,3]-dioxolane was continued at such a rate that the temperature was maintained between 35 and 40° C. After the addition was complete the mixture was stirred for 2 hours and then cooled to 5° C. on an ice bath. Cyclohexanone (57.8 g, 580 mmol) was added dropwise while maintaining the temperature below 10° C. The mixture was stirred for 18 hours at room temperature and two third of the THF was removed in vacuo. The residue was poured into a mixture of ammonium chloride (65 g) in ice water (1 liter) and extracted with ethyl acetate. The organic phase was washed with water, dried (magnesium sulphate), filtered and evaporated in vacuo. The residual oil was slurred in petroleum ether to afford 48 g of 1-(4-[1,3]dioxolan-2yl-phenyl)cyclohexanol as a solid.

Workup

  1. additionwas slowly added
  2. customthe reaction
  3. temperaturewas maintained between 35 and 40° C
  4. additionAfter the addition
  5. temperaturewhile maintaining the temperature below 10° C
  6. stirringThe mixture was stirred for 18 hours at room temperature
  7. customtwo third of the THF was removed in vacuo
  8. additionThe residue was poured into a mixture of ammonium chloride (65 g) in ice water (1 liter)
  9. extractionextracted with ethyl acetate
  10. washThe organic phase was washed with water
  11. dry with materialdried (magnesium sulphate)
  12. filtrationfiltered
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-77a4b0c554fe46e2ba28bdcab58669ae
Source dataset
uspto-grants-2004_07
Patent number
US06762318B2

Reaction notes

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