Lithium Hydroxide → 3-Hydroxy-3-(4-methoxyphenyl)propanoic acid

HRID 133793

Reaction equation

HRID 133793 reaction equation
[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Li+]>C1COCC1>[OH:1][CH:2]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11096232Ethyl 3-hydroxy-3-(4-methoxyphenyl)propanoate

Product 1

HCID 149273073-Hydroxy-3-(4-methoxyphenyl)propanoic acidYield 92.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-hydroxy-3-(4-methoxyphenyl)propanoate (252 mg, 1.1 mmol) in THF (1.1 mL) was added 1 N lithium hydroxide (1.1 mL), and the resulting solution was stirred at room temperature for 3 h. Most of the solvents were removed in vacuo, and 1N hydrochloric acid (1.1 mL) was added. The aqueous layer was extrated with ethyl acetate (x3), and the combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo to give the title compound as an off-white solid (200 mg, 91% yield). 1H NMR (400 MHz, CD3OD) δ 2.57-2.63 (m, 1 H) 2.65-2.72 (m, 1 H) 3.29 (s, 8 H) 3.76 (s, 3 H) 4.82 (s, 9 H) 5.01 (dd, J=8.56, 5.29 Hz, 1 H) 6.86 (ddd, J=9.19, 2.77, 2.39 Hz, 2 H) 7.26-7.30 (m, 2 H). HPLC retention time: 1.392 min (method A). MS (ESI) (M+Na)+ 218.92.

Workup

  1. customMost of the solvents were removed in vacuo, and 1N hydrochloric acid (1.1 mL)
  2. additionwas added
  3. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-84c1b332d1df40789a9bc1fdf08ab0ae
Source dataset
uspto-grants-2008_06
Patent number
US07390925B2

Linked notes

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