p-Toluenesulfonic acid → HCID 67715663, compound

HRID 881765Notes

Reaction equation

HRID 881765 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:18])[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(O)(C1C=CC(C)=CC=1)(=O)=O>CC(C)=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([OH:18])[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 99957018-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 67715663HCID 67715663, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-ol (0.99 g, 3.2 mmol) in acetone (10 mL) and water (5 mL) was added Ts-OH (12 mg, 0.063 mmol) and the reaction was let stir in at 75° C. oil bath for 1 hr. The resulting reaction mixture was cooled to rt and the acetone was removed by rotary evaporation in vacuo. The resulting aqueous mixture was extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated by rotary evaporation in vacuo to afford 0.9 g of a crude pale yellow solid which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.84-1.98 (m, 2H), 2.06-2.29 (m, 4H), 2.76 (td, J=13.8, 6.3 Hz, 2H), 5.47 (s, 1H), 7.51 (s, 4H). ESI-MS m/z: not ionized [M+H]+, retention time 1.18 min (condition E).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to rt
  3. customthe acetone was removed by rotary evaporation in vacuo
  4. extractionThe resulting aqueous mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation in vacuo

Sources & evidence

ORD record
ord-722df797125a4cc6858db94dfcbbbea9
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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