Ammonia → 5-Hydroxy-2-tetralone

HRID 263318Notes

Reaction equation

HRID 263318 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([OH:13])=[CH:8][CH:7]=[CH:6]2.N.[Li]>C(O)C>[OH:13][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH2:11][CH2:12][C:3](=[O:2])[CH2:4]2

Participants

5

Reactant 3

HCID 222AmmoniaHCID 3028194LithiumHCID 110084166-Methoxynaphthalen-1-ol

Product 1

HCID 51035275-Hydroxy-2-tetralone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred slurry of 8.0 g. (0.048 mole) of 6-methoxy-1-naphthol and 200 ml. of liquid ammonia held below the reflux temperature by external cooling there is added 1.05 g. (0.15 g. - atom) of lithium ribbon over 25 minutes. After a further 10 minutes at this temperature, 20 ml. of ethanol is added over 30 minutes. As the blue color fades, the ammonia is evaporated and the residue stirred overnight under nitrogen wth 50 ml. of water, 50 ml. of tetrahydrofuran and 35 ml. of conc. hydrochloric acid. Extraction with three 100 ml. portions of chloroform followed by drying and solvent removal gives 7.24 g. of solid. Recrystallization (4:1) hexane-ethyl acetate gives 5.04 g. (68%) of ketone, m.p. 168°-171° (lit m.p. 155°-162° dec.), JACS 80, 2887 (1958).

Workup

  1. temperatureby external cooling there
  2. additionis added 1.05 g
  3. customAs the blue color fades, the ammonia is evaporated
  4. extractionExtraction with three 100 ml
  5. customby drying
  6. customsolvent removal
  7. customgives 7.24 g
  8. customRecrystallization (4:1) hexane-ethyl acetate
  9. customgives 5.04 g

Sources & evidence

ORD record
ord-4a616405c5004fc5b82e43ed1a3b073a
Source dataset
uspto-grants-1979_05
Patent number
US04156789

Reaction notes

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