Hydrochloric Acid → HCID 14100559, compound

HRID 1198897Notes

Reaction equation

HRID 1198897 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]3[C:22]([OH:24])=[O:23])=[O:15])[CH:5]=[CH:4][C:3]1=2.Cl>[Zn].C(O)(=O)C>[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]([OH:15])[CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]3[C:22]([OH:24])=[O:23])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14100549HCID 14100549, compound

Product 1

HCID 14100559HCID 14100559, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 3.42 g (10 mmoles)of 2-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) carbonyl]cyclohexane carboxylic acid, described in Example III, and 10 g of powdered zinc (0.15 mole)in 150 cm3 of a 2.5M aqueous soda solution is heated at reflux for 7 hours. After cooling to +5° C., the reaction mixture is neutralized with 60 cm3 of 6N HCl and then acidified to pH of about 3 by the addition of 20 cm3 of glacial acetic acid. The mixture is then extracted with ethyl ether [2×150 cm3). The ether phase is thoroughly washed with water, dried on sodium sulfate and evaporated to dryness. The resulting solid is taken up in 50 cm3 of hexane, filtered, washed again twice with 40 cm3 of hexane and dried under a vacuum at 40° C. 2.9 g of 2-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) hydroxymethyl]cyclohexane carboxylic acid are obtained in the form of a white solid whose melting point is 186° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 7 hours
  3. temperatureAfter cooling to +5° C.
  4. extractionThe mixture is then extracted with ethyl ether [2×150 cm3)
  5. washThe ether phase is thoroughly washed with water
  6. customdried on sodium sulfate
  7. customevaporated to dryness
  8. filtrationfiltered
  9. washwashed again twice with 40 cm3 of hexane
  10. customdried under a vacuum at 40° C

Sources & evidence

ORD record
ord-fda4d7b9e0c24aa383e76b3f22589aae
Source dataset
uspto-grants-1990_02
Patent number
US04898864

Reaction notes

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