Sodium borohydride → 9-Hydroxymethyl-9,10-dihydro-9,10-methanoanthracene

HRID 2198646

Reaction equation

HRID 2198646 reaction equation
[CH:1]([C:3]12[CH2:17][CH:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=31)[C:9]1[C:4]2=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:2].[BH4-].[Na+]>CO.O>[OH:2][CH2:1][C:3]12[CH2:17][CH:10]([C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=31)[C:11]1[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 124041419,10-Methanoanthracene-9(10H)-carbaldehyde

Product 1

HCID 130690829-Hydroxymethyl-9,10-dihydro-9,10-methanoanthracene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 9-formyl-9,10-dihydro-9,10-methanoanthracene (200 mg) and sodium borohydride (60 mg) in methanol (5 ml) was stirred at room temperature for 30 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give 9-hydroxymethyl-9,10-dihydro-9,10-methanoanthracene. M.P. 165°-166° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b4b5c81661214b2ab17ab7850509a70e
Source dataset
uspto-grants-1982_11
Patent number
US04358620

Linked notes

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