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Chemical Structure| 52154-82-2 Chemical Structure| 52154-82-2

Structure of 52154-82-2

Chemical Structure| 52154-82-2

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Product Details of [ 52154-82-2 ]

CAS No. :52154-82-2
Formula : C10H16O
M.W : 152.23
SMILES Code : C=C([C@H]1C=C[C@](C)(O)CC1)C
MDL No. :N/A

Safety of [ 52154-82-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P264-P280-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of [ 52154-82-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 52154-82-2 ]

[ 52154-82-2 ] Synthesis Path-Downstream   1~5

  • 3
  • [ 5989-27-5 ]
  • [ 99-48-9 ]
  • [ 18383-51-2 ]
  • [ 52154-82-2 ]
  • [ 22972-51-6 ]
  • [ 2102-62-7 ]
  • [ 10374-04-6 ]
  • 4
  • [ 22972-51-6 ]
  • [ 52154-82-2 ]
  • 5
  • [ 52154-82-2 ]
  • [ 56469-10-4 ]
  • [ 108-24-7 ]
  • [ 61597-29-3 ]
YieldReaction ConditionsOperation in experiment
77% To a reactor were charged ultrapure DMHR (1 .22 kg, 1 equiv.), TsOHH20 (20.7 g, 0.02 equiv.) and toluene (6.71 kg, 7.74 L, 6.3 vol.). While maintaining the batch temperature at 33 to 37 C, a solution of PMD (865 g, 1 .1 equiv.) in toluene (1 .16 kg, 1 .34 L, 1 .1 vol.) was added over 90 mins, followed by a toluene rinse (0.37 kg, 0.42 L, 0.35 vol.). The batch was agitated for 1 hour, then heated to 50-80 C under partial vacuum, using a Dean-Stark trap to remove water by azeotropic distillation. Once drying was complete, TsOHH20 (20.7 g, 0.02 equiv.) was charged and the batch agitated at 70-80 C for 16 hours. Pyridine (543 g, 553 mL, 1 .3 equiv.) was charged to the batch with a toluene (214 g, 246 mL, 0.2 vol.) rinse, followed by acetic anhydride (690 g, 638 mL, 1 .3 equiv.) with a toluene (104 g, 120 mL, 0.1 vol.) rinse, each added over 30 mins while maintaining the batch temperature at 70-80 C. After 20 hours water (9.77 kg, 9.77 L, 8 vol.) was added and the batch temperature was adjusted to 50-60 C. The organic layer was further washed with two portions of water (each 2.44 kg, 2.44 L, 2.0 vol.) at 50-60 C. The batch was concentrated under reduced pressure at < 80 C to about 1 .5 L and IPA (4.80 kg, 6.1 0 L, 5 vol. equiv.) was added. The partial concentration was repeated twice more with another IPA recharge in between. IPA (8.64 kg, 1 1 .0 L, 9.0 vol.) was added and the batch temperature adjusted to 45-55 C. Water (3.1 1 kg, 3.1 1 L, 2.55 vol.) was added, and the batch held at temperature for an hour before cooling to 25 C over an hour. The batch was held at this temperature for over 14 hours, then cooled to 0 to 10 C over an hour and held there for another hour before filtering it, washing the cake with a chilled solution of water (1 .59 kg, 1 .59 L. 1 .3 vol.) in IPA (5.00 kg, 6.35 L, 4.0 vol.). The product was dried under reduced pressure at 45-55 C to afford 1 .54 kg of Compound (13) (99.53% purity by HPLC, 77% yield).
 

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