Hydrochloric Acid → HCID 70359948, compound

HRID 1758156Notes

Reaction equation

HRID 1758156 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C@@H:7]([CH2:10][CH2:11][CH2:12][OH:13])[C@H:6]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][C:15]=3[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:5]2)[O:3]C1.Cl>O1CCCC1>[CH2:29]([O:28][C:15]1[CH:16]=[C:17]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:18]=[CH:19][C:14]=1[C@H:6]1[C@H:7]([CH2:10][CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][C:4](=[O:3])[CH2:5]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86738783HCID 86738783, compound

Product 1

HCID 70359948HCID 70359948, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.17 g. (10.6 mmole) of trans-3-(2,4-dibenzyloxyphenyl)-4-(3-hydroxypropyl)cyclohexanone ethylene ketal, 50 ml. 1 N hydrochloric acid and 100 ml. tetrahydrofuran was heated at reflux for one hour. The reaction was cooled, partially evaporated on a rotovapor and the residue diluted with 300 ml. saturated sodium chloride-300 ml. ether. The ether extract was washed with 300 ml. saturated sodium bicarbonate, dried over magnesium sulfate and evaporated. The residue was crystallized from diisopropyl ether to yield 4.32 g. (92%) of the title compound.

Workup

  1. additionA mixture of 5.17 g
  2. temperatureat reflux for one hour
  3. temperatureThe reaction was cooled
  4. custompartially evaporated on a rotovapor
  5. additionthe residue diluted with 300 ml
  6. extractionThe ether extract
  7. washwas washed with 300 ml
  8. dry with materialsaturated sodium bicarbonate, dried over magnesium sulfate
  9. customevaporated
  10. customThe residue was crystallized from diisopropyl ether
  11. customto yield 4.32 g

Sources & evidence

ORD record
ord-052f1e8fe7d04f3f8617029e25c8252f
Source dataset
uspto-grants-1983_02
Patent number
US04371720

Reaction notes

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