Hydrochloric Acid → HCID 178455789, compound

HRID 1674440Notes

Reaction equation

HRID 1674440 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([O:11]C)=[O:10])[CH2:5][CH2:4]1)=[CH2:2].[OH-].[Na+].Cl.CCCCCC>CO>[CH:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1)=[CH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 14798Sodium HydroxideHCID 153460734-Vinylcyclohexyl formic acid methyl ester

Product 1

HCID 178455789HCID 178455789, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

55.3 g of methyl 4-vinylcyclohexane carboxylate was dissolved in 60 mL of methanol, and was cooled to 15° C. Then, 100 g of 20% sodium hydroxide aqueous solution was added thereto. The solution was further stirred at room temperature for 2 hours, and then concentrated hydrochloric acid was added to make the system acidic. Extraction was performed with hexane, and then the organic layer was washed with saturated saline. The resultant product was dried over anhydrous sodium sulfate, and concentrated, to obtain 52.4 g of reaction mixture. 23.0 g of trans-4-vinylcyclohexane carboxylic acid was obtained by recrystallization from hexane.

Workup

  1. extractionExtraction
  2. washthe organic layer was washed with saturated saline
  3. dry with materialThe resultant product was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto obtain
  6. custom52.4 g of reaction mixture

Sources & evidence

ORD record
ord-11fb6f9d4b684628bb75ad473d2fd2be
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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