Lithium hydroxide, monohydrate → HCID 10707604, compound

HRID 842624Notes

Reaction equation

HRID 842624 reaction equation
C([O:3][C:4](=[O:22])/[C:5](/[CH3:21])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:8]=1)C.O[Li].O>>[CH:16]1([O:15][C:9]2[CH:8]=[C:7](/[CH:6]=[C:5](\[CH3:21])/[C:4]([OH:22])=[O:3])[CH:12]=[CH:11][C:10]=2[O:13][CH3:14])[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10685933HCID 10685933, compound

Product 1

HCID 10707604HCID 10707604, compoundYield 66.8%

Procedure

A suspension of (E)-3-(3-cyclopentoxy-4-methoxyphenyl)-2-methyl-acrylic acid ethyl ester (30 g, 98.6 mmol) and LiOH.H2O (lithium hydroxide hydrate) (5.0 g, 119.2 mmol, 1.2 equiv.) in methanolwater (4:1, 100 mL) was stirred at room temperature for 24 hours. Methanol wag removed under reduced pressure and the resulting residue was dissolved in water (100 mL), washed with three 100 mL portions of ethyl acetate, neutralized with 1.0 N HCl (hydrochloric acid) (100 mL), and extracted with two 150 mL portions of ethyl acetate. The extract was washed with brine, dried over anhydrous Na2SO4 (sodium sulfate), and concentrated under reduced pressure to afford the desired product as a light yellow powder (18.2 g, 66% yield). 1H NMR (300 MHz, CDCl3) δ (ppm): 12.4 (br. s, 1H, COOH), 7.56 (s, 1H, olefinic), 7.04 (m, 1H, aromatic), 4.81 (m, 1H), 3.78 (s, 3H, OCH3), 2.06 (s, 3H, CH3), 1.91-1.57 (m, 8H, cyclopentyl)

Workup

  1. customMethanol wag removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water (100 mL)
  3. washwashed with three 100 mL portions of ethyl acetate
  4. extractionextracted with two 150 mL portions of ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous Na2SO4 (sodium sulfate)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc04be2e86c04da79b0f769fbde52911
Source dataset
uspto-grants-2002_04
Patent number
US06376489B1

Reaction notes

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