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

HRID 2198649Notes

Reaction equation

HRID 2198649 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-df3ed6d0440b4ff1af33bb5dbca864b0
Source dataset
uspto-grants-1982_11
Patent number
US04358620

Reaction notes

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