Citric Acid → 1-(4-(6-Benzyloxy-2-naphthyloxy)phenyl)ethan-1-one

HRID 480262Notes

Reaction equation

HRID 480262 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][CH:5]=1)=[O:3].[CH2:11]([O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([OH:29])[CH:23]=[CH:22]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C(=O)C>[CH2:11]([O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][CH:6]=1)[CH:23]=[CH:22]2)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 144964736-(Benzyloxy)naphthalen-2-OL

Product 1

HCID 224849091-(4-(6-Benzyloxy-2-naphthyloxy)phenyl)ethan-1-oneYield 96%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

4-Fluoroacetophenone (969 μl, 8.00 mmol) was added to dry N,N-dimethylacetamide (12 ml) solution of 6-benzyloxy-2-naphthol (500 mg, 2.00 mmol) and potassium carbonate (553 mg, 4.00 mmol) in nitrogen atmosphere and stirred at 150° C. for 5 hours. After completing the reaction, 10% citric acid was added to the reaction liquid, extracted with methylene chloride, washed with water, dried with magnesium sulfate and concentrated. The obtained residue was purified by silica gel chromatography to obtain the subject compound (707 mg, 1.92 mmol). The result of 1H-NMR was consistent with the above structure.

Workup

  1. additionwas added to the reaction liquid
  2. extractionextracted with methylene chloride
  3. washwashed with water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-da138d5254294875b31f095142a92c7c
Source dataset
uspto-grants-2003_11
Patent number
US06649656B1

Reaction notes

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