Lithium Hydroxide → 4-((1R,2R)-2-hydroxycyclopentyloxy)-3-methoxybenzoic acid

HRID 2204177Notes

Reaction equation

HRID 2204177 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]=1[O:18][CH3:19].[Li+].[OH-]>O1CCOCC1.C(OCC)(=O)C>[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[O:18][CH3:19]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58550939methyl 4-((1R,2R)-2-hydroxycyclopentyloxy)-3-methoxybenzoate

Product 1

HCID 585510384-((1R,2R)-2-hydroxycyclopentyloxy)-3-methoxybenzoic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-[(1R,2R)-2-hydroxycyclopentoxy]-3-methoxy-benzoate (2.8 g, 11 mmol) and LiOH (21 mL of 2.0 M, 42 mmol) in dioxane (20 mL) was stirred at 50° C. overnight. The mixture was diluted with ethyl acetate and was washed with water. The aqueous layer was acidified with 1N HCl and the product was extracted into ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated to give 4-((1R,2R)-2-hydroxycyclopentyloxy)-3-methoxybenzoic acid. ESI-MS m/z talc. 252.1, found 253.5 (M+1)+; Retention time: 1.07 minutes (3 min run).

Workup

  1. washwas washed with water
  2. extractionthe product was extracted into ethyl acetate
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6c816108a4dc4694871d23ad118952f6
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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