Lithium hydroxide, monohydrate → HCID 23404732, compound

HRID 1987274Notes

Reaction equation

HRID 1987274 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][C:10](=[CH2:15])[C:11]([O:13]C)=[O:12].O.[OH-].[Li+]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][C:10](=[CH2:15])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 13674974HCID 13674974, compound

Product 1

HCID 23404732HCID 23404732, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(2-methoxyphenyloxy)propenoate (0.30 g, 1.4 mmol) in THF (30 mL) and water (30 mL) was added lithium hydroxide monohydrate 0.17 g, 4.0 mmol). After stirring at room temperature overnight, the reaction was quenched by addition of concentrated hydrochloric acid (final pH=2), and the product was extracted with EtOAc (3×100 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.42 (ddd, 1H), 7.22 (dd, 1H), 7.10 (dd, 1H), 6.97 (ddd, 1H), 5.48 (d, 1H), 4.51 (d, 1H), 3.64 (s, 3H).

Workup

  1. customthe reaction was quenched by addition of concentrated hydrochloric acid (final pH=2), and the product
  2. extractionwas extracted with EtOAc (3×100 mL)
  3. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ea859cdce8454a72a3e66fb13b5ddeaa
Source dataset
uspto-grants-2009_06
Patent number
US07550489B2

Reaction notes

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