Benzyl Bromide → Benzyl 3-hydroxytetradecanoate

HRID 24982Notes

Reaction equation

HRID 24982 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][CH3:17])[CH2:3][C:4]([OH:6])=[O:5].C(N(CC)CC)C.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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][CH3:17])[CH2:3][C:4]([O:6][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:5]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 16064(+-)-3-Hydroxytetradecanoic acid

Product 1

HCID 10520747Benzyl 3-hydroxytetradecanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxymyristic acid (5.00 g) and triethylamine (2.85 g) in DMF (50 ml) was added benzyl bromide (2.43 ml) and the mixture was stirred at room temperature overnight. After the solvent was removed in vacuo, to the residue were added ethyl acetate and water. The separated ethyl acetate layer was washed twice with water and then dried over anhydrous sodium sulfate. After the ethyl acetate was removed in vacuo, purification was carried out by a silica gel column chromatography (silica gel 30 g, chloroform:methanol=100:0-10) to afford 3.69 g of benzyl 3-hydroxymyristate.

Workup

  1. customAfter the solvent was removed in vacuo, to the residue
  2. additionwere added ethyl acetate and water
  3. washThe separated ethyl acetate layer was washed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the ethyl acetate was removed in vacuo, purification

Sources & evidence

ORD record
ord-e8fb2a66ea7c487f8f69063cb844a64a
Source dataset
uspto-grants-2005_02
Patent number
US06858585B1

Reaction notes

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