Hydrochloric Acid → HCID 70359885, compound

HRID 1762229Notes

Reaction equation

HRID 1762229 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]([C:20]([CH3:28])([CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][C:15]=3[OH:29])[CH2:5]2)[O:3]C1.Cl.O1CCCC1.[Cl-].[Na+]>CCOCC>[CH3:28][C:20]([C:17]1[CH:18]=[CH:19][C:14]([C@H:6]2[C@H:7]([CH2:10][CH2:11][CH2:12][OH:13])[CH2:8][CH2:9][C:4](=[O:3])[CH2:5]2)=[C:15]([OH:29])[CH:16]=1)([CH3:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 86738781HCID 86738781, compound

Product 1

HCID 70359885HCID 70359885, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4.0 g. (9.56 mmoles) of trans-3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-(3-hydroxypropyl)-cyclohexanone ethylene ketal, 50 ml. of 2N hydrochloric acid and 100 ml. of tetrahydrofuran was heated at reflux for 2 hours. The reaction was cooled and added to 500 ml. saturated sodium chloride and 250 ml. ether. The ether extract was separated and washed once with 500 ml. saturated sodium chloride, once with 500 ml. saturated sodium bicarbonate, dried over magnesium sulfate and evaporated (aspirator) to an oil. The crude oil was purified via column chromatography on 200 g. of silica gel eluted with 80% ether-hexane to yield 2.93 g. (82%) of the title compound as an oil.

Workup

  1. additionA mixture of 4.0 g
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction was cooled
  4. additionadded to 500 ml
  5. extractionThe ether extract
  6. customwas separated
  7. washwashed once with 500 ml
  8. dry with materialsaturated sodium bicarbonate, dried over magnesium sulfate
  9. customevaporated (aspirator) to an oil
  10. customThe crude oil was purified via column chromatography on 200 g
  11. washof silica gel eluted with 80% ether-hexane
  12. customto yield 2.93 g

Sources & evidence

ORD record
ord-3bf29bf2c9c04b159485ddc5b8917857
Source dataset
uspto-grants-1989_05
Patent number
US04831059

Reaction notes

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