Hydrochloric Acid → 3-Bromo-7-(hydroxymethyl)-phenanthrene

HRID 1614319Notes

Reaction equation

HRID 1614319 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[C:10]([CH2:16][O:17]C(=O)C)[CH:9]=3.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.Cl>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[C:10]([CH2:16][OH:17])[CH:9]=3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 151591383-Bromo-7-(acetoxymethyl)phenanthreneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 151591393-Bromo-7-(hydroxymethyl)-phenanthreneYield 99.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-bromo-7-(acetoxymethyl)-phenanthrene (2.042 g, 6.20 mmol) in 50 ml of THF was cooled to 0° C. and a solution of diisobutylaluminum hydride in hexane (1.0M, 14 ml, 14 mmol) was added dropwise. After 30 minutes, the solution was cautiously hydrolyzed with 1N HCl and was then diluted with ethyl acetate and washed successively with 1N HCl, sat. NaHCO3, H2O, and brine. Drying (MgSO4) and evaporation gave 1.77 g (99%) of the title compound as a white solid which was used in the next reaction without purification.

Workup

  1. washwashed successively with 1N HCl, sat. NaHCO3, H2O, and brine
  2. customDrying
  3. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-33b1952562494a92b1e5602ca5147c45
Source dataset
uspto-grants-1993_03
Patent number
US05196529

Reaction notes

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