Potassium Hydroxide → HCID 68491472, compound

HRID 1261383Notes

Reaction equation

HRID 1261383 reaction equation
[CH:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[C:5]=1[O:6]/[CH:7]=[CH:8]/[C:9]([O:11]CC)=[O:10])([CH3:3])[CH3:2].[OH-].[K+]>O.C(O)C>[CH:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[C:5]=1[O:6]/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86643149HCID 86643149, compound

Product 1

HCID 68491472HCID 68491472, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Ethyl (E)-3-(2,6-diisopropylphenoxy)acrylate (250 mg, 0.91 mmol) was combined with 0.5 g of solid KOH in 10 mL of a mixture of water/ethanol (20:80), and the mixture was refluxed overnight. The solvent was removed under reduced pressure. The residue was acidified with 5% HCl solution and then extracted with three 25 mL portions of ethyl acetate. The ethyl acetate solution was extracted with saturated sodium chloride solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to yield 150 mg (60%) of (E)-3-(2,6-diisopropylphenoxy)acrylic acid 30b. 1H NMR (400 MHz, CDCl3) 1.17-1.19 (d, 12H), 2.98-3.05 (m, 2H), 5.05-5.08 (d, 1H, J=12.4 Hz), 7.14-7.22 (m, 3H), 7.81-7.85 (d, 1H, J=12.4 Hz). MS (ESI): 271 [M+Na].

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe solvent was removed under reduced pressure
  3. extractionextracted with three 25 mL portions of ethyl acetate
  4. extractionThe ethyl acetate solution was extracted with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-25552f4c24424919b5c29ccaf5bd48f0
Source dataset
uspto-grants-2013_06
Patent number
US08470861B2

Reaction notes

Loading…