Hydrochloric Acid → HCID 22412484, compound

HRID 439656Notes

Reaction equation

HRID 439656 reaction equation
C([O:4][C:5]1[C:18]2[CH:17]=[C:16]([O:19][CH3:20])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[C:8]([CH3:21])=[C:7]([C:22]([O:24][CH3:25])=[O:23])[CH:6]=1)(=O)C.Cl>CO>[OH:4][C:5]1[C:18]2[CH:17]=[C:16]([O:19][CH3:20])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[C:8]([CH3:21])=[C:7]([C:22]([O:24][CH3:25])=[O:23])[CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22412497HCID 22412497, compound

Product 1

HCID 22412484HCID 22412484, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The oil from Step 3 containing 1-acetoxy-9-methoxy-3-methoxycarbonyl-4-methylphenanthrene (77.0 grams, 0.236 mole) was added to a reaction flask containing one mL of concentrated hydrochloric acid in 300 mL of methanol. The reaction mixture was refluxed for 3 hours. The methanol was removed under vacuum and the crude product was purified on a silica gel column using a 1:4 ratio of ethyl acetate:hexane as the eluant. The product was crystallized from methanol and collected by vacuum filtration to yield 15.0 grams of 1-hydroxy-9-methoxy-3-methoxycarbonyl-4-methylphenanthrene.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customThe methanol was removed under vacuum
  3. customthe crude product was purified on a silica gel column
  4. customThe product was crystallized from methanol
  5. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-a8e48577534f46ccb3ab08d8fdcf2179
Source dataset
uspto-grants-1996_05
Patent number
US05514817

Reaction notes

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