Hydrochloric Acid → HCID 54170467, compound

HRID 1031621Notes

Reaction equation

HRID 1031621 reaction equation
[CH3:1][C:2]([CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:3][C:4]([O:6]CC)=[O:5].[OH-].[K+].Cl>C(O)(C)C>[CH3:1][C:2]([CH:9]=[CH:10][CH:11]=[C:12]([CH3:24])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 54061438HCID 54061438, compound

Product 1

HCID 54170467HCID 54170467, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 8.0 g. of the ethyl 3,7,11,15-tetramethyl-2,4,6,14-hexadecatetraenoate obtained in the previous Preparation Example 1 was added to a solution of 3.2 g. of potassium hydroxide in 20 ml. of isopropyl alcohol, and the mixture was stirred at 50° C. for 1 hour. The reaction liquid was then poured into ice-water, made acidic by addition of hydrochloric acid, and extracted with 50 ml. of diethyl ether. The ether phase was washed with water, dried over magnesium sulfate, and concentrated to give 7. g. of an oil. The oil was dissolved in 40 ml. of n-hexane and crystallized at -20° C. to give 3.1 g. of the desired product as white crystals.

Workup

  1. additionwas added to a solution of 3.2 g
  2. customThe reaction liquid
  3. extractionextracted with 50 ml
  4. washThe ether phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give 7
  8. dissolutionThe oil was dissolved in 40 ml
  9. customof n-hexane and crystallized at -20° C.
  10. customto give 3.1 g

Sources & evidence

ORD record
ord-b23d3b75360f4ed5a6aa022ee65a6743
Source dataset
uspto-grants-1990_09
Patent number
US04954525

Reaction notes

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