Ammonia → 1-Methoxy-4-(4-hydroxybutyl)cyclohexa-1,4-diene

HRID 1494094Notes

Reaction equation

HRID 1494094 reaction equation
N.[OH:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[Na]>C(O)C>[CH3:14][O:13][C:10]1[CH2:11][CH:12]=[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][OH:2])[CH2:8][CH:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 976604-(4-Methoxyphenyl)butan-1-olHCID 5360545Sodium

Product 1

HCID 103523271-Methoxy-4-(4-hydroxybutyl)cyclohexa-1,4-diene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ammonia (75 mL) is liquified in a flask at -40° and a solution of 5 g (28 mmol) of p-(4-hydroxybutyl)anisole in 25 mL ethanol is added. 2.76 g (0.12 mmol) of sodium is added in small pieces over 1 hour. The blue solution is then stirred at -40° for 10 minutes during which time the solution decolorizes with the formation of a white precipitate. The reaction is quenched using 5.88 g solid ammonium chloride followed by 25 mL water. The solvent is evaporated under a stream of nitrogen and then poured into brine and extracted with ether (4×100 mL). The organic extracts are combined, dried, filtered and subjected to evaporation to give 1-methoxy-4-(4-hydroxybutyl)cyclohexa1,4-diene as an oil.

Workup

  1. customThe reaction is quenched
  2. customThe solvent is evaporated under a stream of nitrogen
  3. additionpoured into brine
  4. extractionextracted with ether (4×100 mL)
  5. customdried
  6. filtrationfiltered
  7. customsubjected to evaporation

Sources & evidence

ORD record
ord-68b821aaab3e4e65ba13300546bc3354
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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