Hydrochloric Acid → HCID 70359948, compound

HRID 1650051Notes

Reaction equation

HRID 1650051 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. 1N 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-2639c59dc7b04e9c96c118fbedfedf59
Source dataset
uspto-grants-1990_05
Patent number
US04921994

Reaction notes

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