Methanol → Methyl 16-bromohexadecanoate

HRID 1278384Notes

Reaction equation

HRID 1278384 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].S(=O)(=O)(O)O.[CH3:25]O>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:25])=[O:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 62039716-Bromohexadecanoic acid

Product 1

HCID 2736822Methyl 16-bromohexadecanoate

Procedure

A mixture of 22 g. of 16-bromohexadecanoic acid and 200 ml. of methanol is treated with 1.0 ml. of concentrated sulfuric acid and stirred under reflux for 24 hours. The mixture is treated with 10 g. of sodium acetate and the solvent is evaporated. The residue is partially soluble in 300 ml. of ether and the mixture is filtered. The ether solution is dried over magnesium sulfate and evaporated. The residue is crystallized from petroleum ether to yield methyl 16-bromohexadecanoate as a white solid.

Workup

  1. additionA mixture of 22 g
  2. temperatureunder reflux for 24 hours
  3. additionThe mixture is treated with 10 g
  4. customof sodium acetate and the solvent is evaporated
  5. filtrationof ether and the mixture is filtered
  6. dry with materialThe ether solution is dried over magnesium sulfate
  7. customevaporated
  8. customThe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-da33242624b84bc7b1145a7ccb7aca29
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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