Monobenzone → HCID 22120987, compound

HRID 1274363Notes

Reaction equation

HRID 1274363 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[N+:31]([O-:33])=[O:32]>O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[N+:31]([O-:33])=[O:32])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 251404-Chloro-3-nitroanisoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 22120987HCID 22120987, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-(benzyloxy)phenol (2.00 g, 10 mmol) in N,n-dimethylformamide (20 ml) was added potassium tert-butoxide (1.12 g, 10 mmol), followed by stirring for 10 minutes. To the reaction solution was added 4-chloro-3-nitroanisole (1.88 g, 10 mmol), followed by stirring at 150° C. for 6 hours. After allowing to stand overnight, the reaction solution was poured into water and extracted with ethyl acetate. After drying subsequent to washing with water and a saturated aqueous sodium chloride solution, the solvent was evaporated under reduced pressure. The resulting crude crystals were recrystallized from ethanol to give 4-[4-(benzyloxy)phenoxy]-3-nitroanisole (2.13 g).

Workup

  1. stirringby stirring at 150° C. for 6 hours
  2. waitto stand overnight
  3. extractionextracted with ethyl acetate
  4. customAfter drying subsequent
  5. washto washing with water
  6. customa saturated aqueous sodium chloride solution, the solvent was evaporated under reduced pressure
  7. customThe resulting crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-db8ecbea04834bf793aaf0b19eec18c9
Source dataset
uspto-grants-2000_12
Patent number
US06156801

Reaction notes

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