Hydrochloric Acid → SR 11217

HRID 399699Notes

Reaction equation

HRID 399699 reaction equation
[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=3)=[C:15]([CH3:17])[CH3:16])[CH:5]=[CH:4][C:3]1=2.[OH-].[K+].Cl>CO>[CH3:1][C:2]1([CH3:28])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=3)=[C:15]([CH3:16])[CH3:17])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10362193Methyl 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-methyl-1-propenyl]benzoate

Product 1

HCID 3035780SR 11217Yield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of the ester 19 (0.115 g, 0.304 mmol) in 75% aqueous methanol (3 mL) was added one pellet of potassium hydroxide (0.12 g), The mixture was stirred at 75° C. for 1 h during which time the material dissolved. The solution was cooled to room temperature, acidified with 1N aqueous hydrochloric acid, and then extracted with 80% ethyl acetate/hexane. The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated to afford the desired acid 20 as a white powder (0.11 g, 99%): m.p. 204°-206° C. The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy.

Workup

  1. dissolutiondissolved
  2. temperatureThe solution was cooled to room temperature
  3. extractionextracted with 80% ethyl acetate/hexane
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f7ed2136e124b37aed532d3a7fb7d1a
Source dataset
uspto-grants-1998_10
Patent number
US05824484

Reaction notes

Loading…