Hydrochloric Acid → HCID 19088039, compound

HRID 1464505Notes

Reaction equation

HRID 1464505 reaction equation
Cl.O1CCCC1.C([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([C:23]1[C:24](=[O:35])[C:25]2[C:30]([C:31](=[O:34])[C:32]=1[CH3:33])=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)C>C(OCC)(=O)C>[OH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([C:23]1[C:24](=[O:35])[C:25]2[C:30]([C:31](=[O:34])[C:32]=1[CH3:33])=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 19088021HCID 19088021, compound

Product 1

HCID 19088039HCID 19088039, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

6N Hydrochloric acid (20 ml) was added to a tetrahydrofuran solution (20 ml) containing 1-acetoxy-6-(3-methyl-1,4-naphthoquinon-2-yl)-6-phenylhexane (2.8 g, 7.2 mmole), followed by stirring for 5 hours with heating at 70° C. After cooling, ethyl acetate was added to the reaction solution, and the organic layer was separated out, washed with water, dried and evaporated under reduced pressure. The residue was chromatographed on a silica gel column, and elution was performed with isopropyl ether-ethyl acetate (1:1), followed by recrystallization of the object compound from isopropyl ether to give 1-hydroxy-6-(3-methyl-1,4-naphthoquinon-2-yl)-6-phenylhexane (2.1 g). Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 1. By following the procedure of this Example, the Compound Nos. 75, 79 and 81 were prepared.

Workup

  1. temperatureAfter cooling
  2. customthe organic layer was separated out
  3. washwashed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on a silica gel column, and elution
  7. customfollowed by recrystallization of the object compound from isopropyl ether

Sources & evidence

ORD record
ord-52639caaf6dd48db86bbca303afa3430
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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