Water → 3,5-Dichloro-4-(cyclopentyloxy)benzoic acid

HRID 62713Notes

Reaction equation

HRID 62713 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:18])[C:11]=1[O:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:5]([O:7]C)=[O:6].[OH-].[Li+].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:18])[C:11]=1[O:12][CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67041559Methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate

Product 1

HCID 670415553,5-Dichloro-4-(cyclopentyloxy)benzoic acidYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate (2) (1.05 g, 3.63 mmol) and lithium hydroxide (174 mg, 7.26 mmol) were combined in THF (10 mL) and water (ca. 1.5 mL) was added dropwise until a solution formed. The resultant mixture was stirred at RT for 12 h. The THF was removed in vacuo and the residue acidified using aqueous HCl (1 M). The resultant precipitate was filtered to afford 3,5-dichloro-4-(cyclopentyloxy)benzoic acid (3) (820 mg, 82%): m/z 273 (M−H)− (ES−).

Workup

  1. customformed
  2. customThe THF was removed in vacuo
  3. filtrationThe resultant precipitate was filtered

Sources & evidence

ORD record
ord-b48e111b80874ccca57698bb1b9316ff
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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