Hydrochloric Acid → HCID 20322257, compound

HRID 372895Notes

Reaction equation

HRID 372895 reaction equation
[C:1]([CH:5]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])(=[O:4])[CH2:2][OH:3].[OH-].[K+].Cl>CO.O>[C:1]([CH:5]([CH2:17][CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:4])[CH2:2][OH:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 20322270HCID 20322270, compound

Product 1

HCID 20322257HCID 20322257, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A clear, yellow solution of ethyl 8-glycoloyl-12-hydroxyheptadecanoate (7.9 g., 0.02 mole) and potassium hydroxide (2.24 g., 0.04 mole) in 90% aqueous methanol (50 ml.) is stirred at 25° under nitrogen for 20 hours. The reaction solution is evaporated in vacuo at 40° leaving a residual red oil which is dissolved in water (200 ml.). The resulting solution is acidified with concentrated hydrochloric acid (10 ml.) and extracted with ether (2 × 200 ml.). The organic extract is washed with saturated brine (2 × 200 ml.), dried over sodium sulfate, filtered and evaporated in vacuo at 40°-50° providing the title compound as a slightly impure, deep yellow oil (6.3 g., 92%).

Workup

  1. customThe reaction solution is evaporated in vacuo at 40°
  2. customleaving a residual red oil which
  3. extractionextracted with ether (2 × 200 ml.)
  4. extractionThe organic extract
  5. washis washed with saturated brine (2 × 200 ml.)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo at 40°-50°

Sources & evidence

ORD record
ord-25fc4f749d234a3a815a2ee165b9ca6d
Source dataset
uspto-grants-1978_05
Patent number
US04092356

Reaction notes

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