Hydrochloric Acid → HCID 9799946, compound

HRID 1739730Notes

Reaction equation

HRID 1739730 reaction equation
C([O:3][C:4](=[O:30])/[CH:5]=[C:6](\[CH3:29])/[CH:7]=[CH:8]/[C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[C:15]1[CH:24]=[CH:23][C:22]2[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=2[CH:16]=1)C.[OH-].[K+].C(Cl)Cl.Cl>CO>[CH3:29]/[C:6](/[CH:7]=[CH:8]/[C:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=1[C:15]1[CH:24]=[CH:23][C:22]2[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=2[CH:16]=1)=[CH:5]\[C:4]([OH:30])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 9887621HCID 9887621, compound

Product 1

HCID 9799946HCID 9799946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixed (15:2) ester product from Example 1 is combined with 5 ml of 2N aqueous potassium hydroxide in 10 ml of methyl alcohol and stirred at reflux temperature for 3 hours. The reaction mixture is cooled to room temperature, poured into a mixture of ice and methylene chloride, and acidified to pH 3 with 3N hydrochloric acid. The organic layers are combined, dried over sodium sulfate and evaporated to give a light yellow solid. The solid is recrystallized form absolute ethyl alcohol to give 0.5 g of the desired compound as colorless crystals.

Workup

  1. temperatureat reflux temperature for 3 hours
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customto give a light yellow solid
  5. customThe solid is recrystallized form absolute ethyl alcohol

Sources & evidence

ORD record
ord-b81432df09804078b4c8590cbc2189ba
Source dataset
uspto-grants-1999_10
Patent number
US05968908

Reaction notes

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