Benzyl Bromide → 5-(Benzyloxy)pentan-1-ol

HRID 1410650Notes

Reaction equation

HRID 1410650 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Al]>C(Cl)Cl>[CH2:8]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 81051,5-PentanediolHCID 5359268Aluminum

Product 1

HCID 2211945-(Benzyloxy)pentan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,5-pentanediol (2.10 mL, 20.0 mmol, 1.0 equiv.) was dissolved in CH2Cl2 (100 mL). Ag2O (6.95 g, 30.0 mmol, 1.5 equiv.) and benzyl bromide (2.62 mL, 22.0 mmol, 1.1 equiv.) were added to the solution sequentially. The flask was wrapped with aluminium foil, and the solution was stirred at room temperature for 18 h. The solution was filtered through a pad of celite, eluting with CH2Cl2, and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, Ethyl Acetate (EtOAc): petroleum ether (pet ether)=3:17 to 1:1) to give the alcohol as a colorless oil. 1H NMR (500 MHz, CDCl3) δ=7.37-7.26 (m, 5H), 4.50 (s, 2H), 3.64 (t, J=6.5 Hz, 2H), 3.49 (t, J=6.5 Hz, 2H), 1.70-1.63 (m, 2H), 1.62-1.55 (m, 2H), 1.50-1.42 (m, 2H), 1.34 (br s, 1H) ppm; 13C NMR (125 MHz, CDCl3) δ=138.8, 128.6, 127.8, 127.7, 73.2, 70.5, 63.1, 32.8, 29.7, 22.7 ppm; Low Resolution Mass Spectrometry (LRMS) (ESI+ve) m/z: 217 (M+Na+).

Workup

  1. filtrationThe solution was filtered through a pad of celite
  2. washeluting with CH2Cl2
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography (silica gel, Ethyl Acetate (EtOAc): petroleum ether (pet ether)=3:17 to 1:1)

Sources & evidence

ORD record
ord-03b2278cb9bd40dba65ba27969f39cd8
Source dataset
uspto-grants-2014_12
Patent number
US08921568B2

Reaction notes

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