Benzyl Bromide → HCID 15948207, compound

HRID 1714756Notes

Reaction equation

HRID 1714756 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=[O:4].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(OC(=O)C)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([O:5][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 94180Hydroxycaprylic Acid

Product 1

HCID 15948207HCID 15948207, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of a commercially available racemic 2-hydroxyoctanoic acid mixture (1.00 g, 6.2 mmol.) in HPLC-grade ethylacetate (30 ml), there are added in succession benzyl bromide (2.22 ml; 18.7 mmol.), triethylamine (2.6 ml, 18.7 mmol.) and tetrabutylammonium iodide (1.15 g; 3.12 mmol.). The solution is stirred for 18 hours at room temperature and the solvent is thereafter evaporated. The residue is taken up into ether and the organic layer is then washed with a saturated solution of NaHCO3 and H2O (2×). The organic layer is dried over MgSO4, filtered and evaporated to yield crude benzyl 2-hydroxyoctanoate (Rf=0.57 in a 3/1 petroleum ether/EtOAc mixture; phosphomolybdinium compound and U.V. color development agent)

Workup

  1. customthe solvent is thereafter evaporated
  2. washthe organic layer is then washed with a saturated solution of NaHCO3 and H2O (2×)
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-4d76da1a69914a4b90585d47b77fba8c
Source dataset
uspto-grants-2010_09
Patent number
US07799762B2

Reaction notes

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