Hydrochloric Acid → HCID 54170467, compound

HRID 542148Notes

Reaction equation

HRID 542148 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

8.0 g. of the ethyl 3,7,11,15-tetramethyl-2,4,6,14-hexadecatetraenoate obtained in the previous. 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. additionExample 1 was 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-d6fae744b8354fc39f1a4b7cd413d34c
Source dataset
uspto-grants-1987_04
Patent number
US04655973

Reaction notes

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