Dichloromethane → 6-Ethenylnaphthalen-2-ol

HRID 734168Notes

Reaction equation

HRID 734168 reaction equation
C(OC([O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]=[CH2:18])[CH:11]=[CH:10]2)C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(Cl)Cl>C(O)C>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([CH:17]=[CH2:18])[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 231357602-Ethenyl-6-(1-ethoxyethoxy)naphthalene

Product 1

HCID 231357586-Ethenylnaphthalen-2-olYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

18 g of 6-(1-Ethoxy ethoxy)-2-vinylnaphthalene (0.0743 mol) was dissolved in 80 mL of ethanol. To this was added 1.6 g of pyridinium p-toluenesulfonate (0.0064 mol). The reaction mixture was stirred at 50° C. After 3 h, TLC analysis (silica, CH2Cl2) indicated that the reaction was over. The reaction mixture was cooled down to room temperature and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, CH2Cl2) to yield 11.15 g of pure 6-hydroxy-2-vinylnaphthalene (62%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product was purified by column chromatography (silica gel, CH2Cl2)

Sources & evidence

ORD record
ord-b0e6acb87795488ba055c2f35d8934ef
Source dataset
uspto-grants-2009_09
Patent number
US07592125B2

Reaction notes

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