Potassium Hydroxide → HCID 11833354, compound

HRID 1857570Notes

Reaction equation

HRID 1857570 reaction equation
[CH2:1]1[O:21][C:20]2[C:3](=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:19]=2)[CH2:7][CH:8]([C:14]([O:16]CC)=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[O:2]1.[OH-].[K+]>C(O)C.O>[CH2:1]1[O:21][C:20]2[C:3](=[CH:4][C:5]([O:22][CH3:23])=[C:6]([CH:19]=2)[CH2:7][CH:8]([C:14]([OH:16])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[O:2]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22131260HCID 22131260, compound

Product 1

HCID 11833354HCID 11833354, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the diethyl 2-(4,5-methylenedioxy-2-methoxybenzyl)-malonate (20.00 g, 0.066 mol) of in ethanol (50 mL) was added a solution of potassium hydroxide (3.50 g, 0.066 mol) in water (25 mL). The solution stirred at reflux for 6 h. After cooling the aqueous layer was washed with ether and acidified with concentrated HCl to pH 1 and extracted with ethyl acetate. The organic extracts were dried (Na2SO4) and concentrated to afford the title compound as a yellow solid (17.30 g, 89%): 1H NMR (400 MHz, CDCl3) δ 10.20 (b, 1H), 6.68 (s, 1H), 6.50 (s, 1H), 5.90 (s, 2H), 4.15 (q, 2H), 3.72 (s, 3H), 3.10 (dd, 2H), 1.20 (t, 3H); MS(ESI) m/e 297.0 [M+H]+.

Workup

  1. temperatureat reflux for 6 h
  2. temperatureAfter cooling the aqueous layer
  3. washwas washed with ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic extracts were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c4d066091f944817bd84807f0081b2e8
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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