Water → 9,10-Dihydrophenanthrene-1-methanol

HRID 544672Notes

Reaction equation

HRID 544672 reaction equation
[C:1]1([C:15](OCC)=[O:16])[C:14]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[C:1]1([CH2:15][OH:16])[C:14]2[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13281335Ethyl 9,10-dihydrophenanthrene-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 132813369,10-Dihydrophenanthrene-1-methanolYield 35.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a dry nitrogen atmosphere a solution of ethyl 9,10-dihydrophenanthrene-1-carboxylate (5.15 grams, 0.02 mole) in anhydrous diethyl ether (50 ml) was added to a slurry of lithium aluminum hydride (0.5 grams, 0.013 mole) in anhydrous diethyl ether (100 ml). The rate was such that a reflux was maintained throughout the addition. After complete addition, the mixture was stirred at room temperature for two hours. Water (1 ml) was cautiously added to the reaction mixture, followed by 10% aqueous sodium hydroxide (1 ml) and water (3 ml). Diatomaceous earth was added to the mixture and the resultant mixture filtered. The filter cake was washed with diethyl ether and the filtrates combined and evaporated under reduced pressure to give a green solid. This solid was chromatographed on silica gel using methylene chloride as eluant to give a brown solid. Recrystallization from n-hexane gave 9,10-dihydrophenanthrene-1-methanol (1.5 grams) as tan crystals (mp 108°-110°).

Workup

  1. temperaturewas maintained throughout the addition
  2. additionAfter complete addition
  3. additionDiatomaceous earth was added to the mixture
  4. filtrationthe resultant mixture filtered
  5. washThe filter cake was washed with diethyl ether
  6. customevaporated under reduced pressure
  7. customto give a green solid
  8. customThis solid was chromatographed on silica gel
  9. customto give a brown solid
  10. customRecrystallization from n-hexane

Sources & evidence

ORD record
ord-7e58b2734d404482bb0a0f217159c56f
Source dataset
uspto-grants-1984_05
Patent number
US04451484

Reaction notes

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