Hydrochloric Acid → HCID 24858722, compound

HRID 1759601Notes

Reaction equation

HRID 1759601 reaction equation
C[Si](C)(C)[O:3][C:4]1([CH3:16])[CH2:13][CH2:12][CH:11]2[C:6](=[CH:7][CH2:8][CH2:9][C:10]2([CH3:15])[CH3:14])[CH2:5]1.C(O)C.Cl>O>[CH3:16][C@@:4]1([OH:3])[CH2:5][C:6]2=[CH:7][CH2:8][CH2:9][C:10]([CH3:14])([CH3:15])[C@@H:11]2[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 20531505HCID 20531505, compound

Product 1

HCID 24858722HCID 24858722, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,2,3,4,4a,5,6,7-octahydro-2-trimethylsilyloxy-2,5,5-trimethylnaphthalene (0.78 g), ethanol (40 ml), water (4 ml) and 2 N hydrochloric acid (1 ml) was stirred at 20°-25° for 17 h. The mixture was poured onto water and extracted with hexanes. The combined organic extracts were washed with sodium bicarbonate solution and the solvent evaporated to give 0.61 g of crude product. Chromatography gave 0.42 g (75%) of α-ambrinol. Spectral and analytical data for this material was consistent with that given in Example 4.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with hexanes
  3. washThe combined organic extracts were washed with sodium bicarbonate solution
  4. customthe solvent evaporated
  5. customto give 0.61 g of crude product

Sources & evidence

ORD record
ord-5896690f7f634385ba2bbcbbab8f2644
Source dataset
uspto-grants-1982_07
Patent number
US04341908

Reaction notes

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