Hydrochloric Acid → HCID 9931852, compound

HRID 1940694Notes

Reaction equation

HRID 1940694 reaction equation
[CH2:1]([C:7]1[C:8](/[CH:21]=[CH:22]/[C:23]2[CH:33]=[CH:32][C:26]([C:27]([O:29]CC)=[O:28])=[CH:25][CH:24]=2)=[CH:9][C:10]2[C:11]([CH3:20])([CH3:19])[CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[C:15]=2[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[K+].O1CCCC1.Cl>C(O)C.O>[CH2:1]([C:7]1[C:8](/[CH:21]=[CH:22]/[C:23]2[CH:33]=[CH:32][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)=[CH:9][C:10]2[C:11]([CH3:19])([CH3:20])[CH2:12][CH2:13][C:14]([CH3:18])([CH3:17])[C:15]=2[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 23002538HCID 23002538, compound

Product 1

HCID 9931852HCID 9931852, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

8 g of this ester were dissolved in 50 ml of ethanol and treated with a solution of 10 g of potassium hydroxide in 10 ml of water and 20 ml of ethanol. After the addition of 50 ml of tetrahydrofuran the mixture was heated to 40° C. for 4 hours. The clear, yellow reaction solution was poured-into a mixture of ice and 6N hydrochloric acid, extracted with ethyl acetate, the organic phase was washed with water, dried and evaporated. After recrystallization of the crystalline residue from hexane/ethyl acetate there were obtained 6.2 g of p-[(E)-2-(3-hexyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)vinyl]benzoic acid in the form of white crystals, melting point 134°-136° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase was washed with water
  3. customdried
  4. customevaporated
  5. customAfter recrystallization of the crystalline residue from hexane/ethyl acetate there

Sources & evidence

ORD record
ord-c5c5735462b0445bac84879ce0b2f391
Source dataset
uspto-grants-1997_12
Patent number
US05700836

Reaction notes

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