Benzyl Bromide → Benzyl 5-hydroxypentanoate

HRID 1656696Notes

Reaction equation

HRID 1656696 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O-:8])=[O:7].[Na+].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CC(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7]

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 236951955-Hydroxypentanoic Acid SodiuM Salt

Product 1

HCID 19788674Benzyl 5-hydroxypentanoateYield 176.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a suspension of 569 mg (4.06 mmol) of sodium 5-hydroxypentanoate 69 in 3 mL of acetone was added 1.39 g (0.97 mL, 8.11 mmol, 2.0 equiv) of benzyl bromide and 65 mg (0.203 mmol, 0.05 equiv) of tetrabutylammonium bromide. The mixture was heated at 45° C. for 24 hours, cooled, and concentrated. The residue was dissolved in 200 mL of ethyl acetate, washed with 50 mL portions of 1N aqueous sodium bisulfate, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give 1.49 g of a pale yellow oil. Purification by MPLC (Lobar C-column, 45% ethyl acetate/hexane) have 641 mg (76%) of the title compound as an oil: 1H NMR (300 MHz, CDCl3) δ7.38-7.26 (m, 5H), 5.12 (s, 2H), 3.64 (t, 2H, J=6.3 Hz), 2.41 (t, 2H, J=7.2 Hz), 1.80-1.71 (m, 2H), 1.64-1.54 (m, 3H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 200 mL of ethyl acetate
  4. washwashed with 50 mL portions of 1N aqueous sodium bisulfate, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ba3e9569207c4ddfae2397e6a9cfd3c3
Source dataset
uspto-grants-1993_10
Patent number
US05254682

Reaction notes

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