Dichloromethane → 6-Ethenylnaphthalen-2-ol

HRID 1295540Notes

Reaction equation

HRID 1295540 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-a41235ba9f0c4316a18616f1cf89631e
Source dataset
uspto-grants-2007_07
Patent number
US07244542B2

Reaction notes

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