Benzyl Bromide → HCID 15948207, compound

HRID 1920606Notes

Reaction equation

HRID 1920606 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-8cc9d91aec84477482df514c063c2e0b
Source dataset
uspto-grants-2012_05
Patent number
US08173133B2

Reaction notes

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