Dichloromethane → 5-Ethylnaphthalen-1-ol

HRID 1727275Notes

Reaction equation

HRID 1727275 reaction equation
ClCCl.C[O:5][C:6]1[C:15]2[C:10](=[C:11]([CH2:16][CH3:17])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.B(Br)(Br)Br>O>[CH2:16]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[CH:8][CH:7]=[C:6]2[OH:5])[CH3:17]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 123363811-Ethyl-5-methoxynaphthalene

Product 1

HCID 123363835-Ethylnaphthalen-1-olYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Anhydrous dichloromethane (20 mL) was added to 8 (870 mg, 4.6 mmol). After cooling to 0° C., BBr3 (boron tribromide 1.0M in dichloromethane) (14 mL, 14 mmol) was added dropwise. The reaction mixture was heated to reflux for 5 h. After cooling, a large amount of water was slowly added and the mixture was extracted three times with dichloromethane. The organic layer was evaporated and the residue was purified on MPLC to afford compound 9c, 75% yield; MS-ESI− (m/z, %): 171 (M+−1, 100), 172 (M+, 45); 1H NMR δ 1.37 (3H, t, J=7.8 Hz, CH3CH2—), 3.10 (2H, q, J=7.8 Hz, CH3CH2—), 5.19 (1H, s, OH), 6.82 (1H, d, J=7.8 Hz, H-2), 7.31-7.45 (3H, m, H-3, 6, 7), 7.65 (1H, d, J=8.7 Hz, H-4), 8.06 (1H, d, J=8.1 Hz, H-8).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted three times with dichloromethane
  5. customThe organic layer was evaporated
  6. customthe residue was purified on MPLC

Sources & evidence

ORD record
ord-64a586c6ac184fb3ba227ce544f60d7f
Source dataset
uspto-grants-2009_02
Patent number
US07495026B2

Reaction notes

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