Hydrochloric Acid → HCID 20322213, compound

HRID 1833761Notes

Reaction equation

HRID 1833761 reaction equation
Cl[C:2]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:3].[BH4-].[Na+].Cl.OCC(CCCC(OC(=O)C)CCCCC)CCCCCCC([O-])=O>COCCOCCOC.O>[OH:3][CH2:2][CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20322197Ethyl 12-(acetyloxy)-8-(chlorocarbonyl)heptadecanoateHCID 20322276HCID 20322276, compound

Product 1

HCID 20322213HCID 20322213, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Procedure

Ethyl 8-chlorocarbonyl-12-acetoxyheptadecanoate (Example 7, Step D) (14.0 g., 0.0335 mole) is added all at once to a solution of sodium borohydride (2.7 g., 0.07 mole) in dry diglyme (75 ml.). An exothermic reaction occurs with foaming and a rise in temperature to 55°. After 2 hours, the reaction mixture is cooled in an ice bath and 10% hydrochloric acid is added dropwise until the mixture is acidic to Congo Red. Water (250 ml.) is then added; the oily product is extracted into ether, washed with after, and dried over sodium sulfate. The ether is evaporated to leave 12.2 g. of 8-hydroxymethyl-12-acetoxyheptadecanoate as a yellow oil. The product is used in the next step without further purification.

Workup

  1. customAn exothermic reaction
  2. customto 55°
  3. temperaturethe reaction mixture is cooled in an ice bath
  4. extractionthe oily product is extracted into ether
  5. washwashed with after, and
  6. dry with materialdried over sodium sulfate
  7. customThe ether is evaporated
  8. customto leave 12.2 g
  9. customThe product is used in the next step without further purification

Sources & evidence

ORD record
ord-137cace0761f4d31a5b472685153f0e9
Source dataset
uspto-grants-1978_01
Patent number
US04066692

Reaction notes

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