1,2-Dichloroethane → HCID 21274863, compound

HRID 414788Notes

Reaction equation

HRID 414788 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:5]=[C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:7]=1[OH:8].[Cl-].[Al+3].[Cl-].[Cl-].CC1C=CC=C(C(C)(C)C)C=1[OH:37].Cl.[CH2:39](Cl)[CH2:40]Cl>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:9]([CH3:12])([CH3:10])[CH3:11])[C:7]=1[OH:8])[C:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:39][CH3:40])=[O:20])=[O:37]

Participants

6

Reactant 5

HCID 111,2-Dichloroethane2×HCID 313Hydrochloric AcidHCID 166782-tert-Butyl-6-methylphenolHCID 6451240Aluminum(III) ChlorideHCID 21274874HCID 21274874, compound

Product 1

HCID 21274863HCID 21274863, compound

Conditions

Temperature
-5 °C

Procedure

7-(3-methyl-5-t-butyl-4-hydroxyphenyl)heptanoic acid.--To a cooled (-5° C.) solution of 103 parts of ethyl 6-chloroformyl hexanoate in 100 parts by volume of ethylene chloride is rapidly added with stirring 133 parts of granular anhydrous aluminum chloride. To this mixture is next added a solution of 88 parts of 2-methyl-6-t-butylphenol in 500 parts by volume of ethylene chloride. The reaction mixture is stirred at -5° C. for 5 hours and then allowed to slowly attain room temperature overnight. At the end of this time the material is poured over ice, rendered acidic with 6N hydrochloric acid and extracted with ether. The combined extracts are successively washed with water, dilute aqueous sodium bicarbonate solution and saturated aqueous sodium bicarbonate solution. After drying over sodium sulfate, the solvent is removed under reduced pressure to yield ethyl 6-(3-methyl-5-t-butyl-4-hydroxybenzoyl)hexanoate, which is saponified with excess potassium hydroxide in methanol. After acidification of the reaction mixture, the solid, comprising 6-( 3-methyl-5-t-butyl-4-hydroxybenzoyl)hexanoic acid, is subjected to a Clemmenson reduction as modified by Martin [J.A.C.S. 58, 1438 (1936)] to yield 7-(3-methyl-5-t-butyl-4-hydroxyphenyl)heptanoic acid which is esterified with ethanol and p-toluenesulfonic acid to yield the corresponding ethyl ester.

Workup

  1. additionis rapidly added
  2. customallowed to slowly attain room temperature overnight
  3. additionAt the end of this time the material is poured over ice
  4. extractionextracted with ether
  5. washThe combined extracts are successively washed with water, dilute aqueous sodium bicarbonate solution and saturated aqueous sodium bicarbonate solution
  6. dry with materialAfter drying over sodium sulfate
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e7507c73dc024532bea3c940de8435dd
Source dataset
uspto-grants-1988_12
Patent number
US04794138

Reaction notes

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