N-bromobutanimide → 4-Hydroxyphenanthrene

HRID 476835Notes

Reaction equation

HRID 476835 reaction equation
O=[C:2]1[C:15]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1.BrN1C(=[O:22])CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH:2]1[C:15]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[C:5]([OH:22])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 2256831-Oxo-1,2,3,4-tetrahydrophenanthrene

Product 1

HCID 821054-Hydroxyphenanthrene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In a 1000 ml 3-neck flask equipped with magnetic stirrer and reflux condenser with nitrogen inlet, 400 ml of carbon tetrachloride was added followed by 26 gms of 4 oxo-1,2,3,4-tetrahydrophenanthrene and 26.5 gm of N-bromo succinimide. The reaction was illuminated with a 600 watt Quartzlite lamp for 6 hours. Then an additional 2.0 gms of N-bromosuccinimide was added and the reaction refluxed for 1 hour. The reaction was cooled to room temperature and the solids filtered off and washed with carbon tetrachloride and air dried. The solids were recrystallized from 220 ml of ethyl acetate, filtered and washed with several portions of warm water, dried in vacuo in the presence of P2O5 to yield 8.3 gms (32.25% by weight) of 4-phenanthrol. m.p. 114°-116° C. m/e 194.

Workup

  1. customIn a 1000 ml 3-neck flask equipped with magnetic stirrer
  2. temperaturereflux condenser with nitrogen inlet
  3. customThe reaction was illuminated with a 600 watt Quartzlite lamp for 6 hours
  4. temperaturethe reaction refluxed for 1 hour
  5. filtrationthe solids filtered off
  6. washwashed with carbon tetrachloride and air
  7. customdried
  8. customThe solids were recrystallized from 220 ml of ethyl acetate
  9. filtrationfiltered
  10. washwashed with several portions of warm water
  11. dry with materialdried in vacuo in the presence of P2O5

Sources & evidence

ORD record
ord-55e807589faf450fb0f153129ca8b5bf
Source dataset
uspto-grants-1989_12
Patent number
US04886733

Reaction notes

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