Benzyl Bromide → Benzyl 3-hydroxyhexadecanoate

HRID 24985Notes

Reaction equation

HRID 24985 reaction equation
[OH:1][CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][C:4]([OH:6])=[O:5].C(N(CC)CC)C.[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[OH:1][CH:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][C:4]([O:6][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:5]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 3015903-Hydroxyhexadecanoic acid

Product 1

HCID 22565043Benzyl 3-hydroxyhexadecanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxyhexadecanoic acid (1.90 g) and triethylamine (0.97 ml) in DMF (20 ml) was added benzyl bromide (0.83 ml) and the mixture was stirred at room temperature for 3 days. After the solvent was removed in vacuo, ethyl acetate and water were added to the residue. The separated ethyl acetate layer was washed twice with water and then dried over anhydrous sodium sulfate. After concentration, the residue was purified by a silica gel column chromatography (silica gel 15 g, chloroform: methanol=100:0-8) to afford 1.22 g of benzyl 3-hydroxyhexadecanoate.

Workup

  1. customAfter the solvent was removed in vacuo, ethyl acetate and water
  2. additionwere added to the residue
  3. washThe separated ethyl acetate layer was washed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter concentration
  6. customthe residue was purified by a silica gel column chromatography (silica gel 15 g, chloroform: methanol=100:0-8)

Sources & evidence

ORD record
ord-cec8999c127e4db0a351f02f2839d401
Source dataset
uspto-grants-2005_02
Patent number
US06858585B1

Reaction notes

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