Ethanol → Ethyl 16-hydroxyhexadecanoate

HRID 1740781Notes

Reaction equation

HRID 1740781 reaction equation
[OH: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.[CH2:25](O)[CH3:26]>>[OH: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][CH2:25][CH3:26])=[O:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1046616-Hydroxyhexadecanoic acid

Product 1

HCID 15153258Ethyl 16-hydroxyhexadecanoate

Procedure

To a solution of 5.0 g of 16-hydroxyhexadecanoic acid in 100 ml of ethanol was added 0.2 ml of sulfuric acid and the mixture was heated under reflux for one hour. The reaction solution was distilled off under reduced pressure. The residue was diluted with ethyl acetate and washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then distilled under reduced pressure to afford the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. distillationThe reaction solution was distilled off under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed successively with water
  6. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-adfe8077c2c7429b8d922bb1973fde0b
Source dataset
uspto-grants-1999_10
Patent number
US05972943

Reaction notes

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