Hydrochloric Acid → HCID 10333572, compound

HRID 1614031Notes

Reaction equation

HRID 1614031 reaction equation
O.Cl.[CH3:3][C:4]1([CH3:23])[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]2[CH:9]=[C:8]([C:16](=O)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:7]=[CH:6][C:5]1=2>C1(C)C=CC=CC=1>[CH3:3][C:4]1([CH3:23])[CH2:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]2[CH:9]=[C:8]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:7]=[CH:6][C:5]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 962Water2×HCID 10469392HCID 10469392, compound

Product 1

HCID 10333572HCID 10333572, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 6 g zin wool and 0.6 g of mercuric chloride, there are added 9 cm3 of water and 0.3 cm3 of 12N HCl. The mixture is stirred for 10 minutes at ambient temperature. The aqueous phase is removed by decanting. The resulting amalgam is rinsed with 20 cm3 of water. There are added 7.21 g (0.025 mole) of 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydo-2-naphthyl)-4-oxo butyric acid, described in Example III, 10 cm3 of water, 8 cm3 of toluene and 5 cm3 of 12N HCl. The mixture is heated for 34 hours at reflux with stirring, adding 3 cm3 of 12N HCl every 6 hours. The reaction mixture is diluted by the addition of 100 cm3 of toluene, filtered (separation of residual amalgam) and rinsed with toluene. The toluene phase is separated, washed copiously with water, dried on sodium sulfate and concentrated under reduced pressure. The resulting crude oil is purified by chromatography on silica 60 gel in a 2/8/90 acetic acid/dioxan/ toluene eluant mixture. After evaporation, the recovered solid is taken up in a minimum of isopropyl ether, filtered and dried under a vacuum at 70° C. 4.6 g of 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) butyric acid in the form of a white solid whose melting point is 99° C. are obtained.

Workup

  1. customThe aqueous phase is removed
  2. customby decanting
  3. washThe resulting amalgam is rinsed with 20 cm3 of water
  4. temperatureThe mixture is heated for 34 hours
  5. temperatureat reflux
  6. stirringwith stirring
  7. filtrationfiltered
  8. custom(separation of residual amalgam)
  9. washrinsed with toluene
  10. customThe toluene phase is separated
  11. washwashed copiously with water
  12. customdried on sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe resulting crude oil is purified by chromatography on silica 60 gel in a 2/8/90 acetic acid/dioxan/ toluene eluant mixture
  15. customAfter evaporation
  16. filtrationfiltered
  17. customdried under a vacuum at 70° C

Sources & evidence

ORD record
ord-486ff53045bf4ab98f9b330c3a025bd1
Source dataset
uspto-grants-1993_03
Patent number
US05194663

Reaction notes

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