Water → 9-beta-Hydroxyethyl-9,10-dihydro-9,10-methanoanthracene

HRID 27961Notes

Reaction equation

HRID 27961 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]12[CH2:20][CH:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=31)[C:12]1[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC.C(OCC)(=O)C>[OH:3][CH2:4][CH2:5][C:6]12[CH2:20][CH:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=31)[C:12]1[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 12507120Ethyl (9,10-methanoanthracen-9(10H)-yl)acetateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 130690859-beta-Hydroxyethyl-9,10-dihydro-9,10-methanoanthracene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (9,10-dihydro-9,10-methano-9-anthryl)-acetic acid ethyl ester (125 mg) and lithium aluminum hydride (80 mg) in ether (6 ml) was stirred at room temperature for 1 hour. Excess lithium aluminum hydride was decomposed by addition of water. The reaction mixture was diluted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated to dryness to give crystals of 9-β-hydroxyethyl-9,10-dihydro-9,10-methanoanthracene. M.P. 99°-100.5° C.

Workup

  1. dry with materialdried over anhydrous sodium sulfate
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-a85fa2be2355424daa43edd90fad36b3
Source dataset
uspto-grants-1980_09
Patent number
US04224344

Reaction notes

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