HCID 22145706, compound → HCID 22145794, compound

HRID 356931Notes

Reaction equation

HRID 356931 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=[O:11])[CH2:5][CH:4]=[CH:3][CH2:2]1.Cl([O-])=[O:18].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.CC(=CC)C>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[C:10]([OH:18])=[O:11])[CH2:2][CH:3]=[CH:4][CH2:5]1

Participants

6

Reactant 3

HCID 22145706HCID 22145706, compoundHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 22145794HCID 22145794, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

A stirred solution of 3-cyclopent-3-enyloxy-4-methoxybenzaldehyde (1.75 g) in t-butanol (36.5 mL) and 2-methyl-2-butene (9.0 mL) is treated dropwise with an aqueous solution (34 mL) containing sodium chlorite (80% technical grade; 1.0 g) and sodium dihydrogen phosphate (8.75 g). The resulting mixture is further stirred for 5 hours, the layers are separated and the aqueous layer is extracted with t-butyl methyl ether (3×30 mL). The combined organic layers are washed with water (2×15 mL), dried over sodium sulfate and the solvent removed under reduced pressure. The resulting residue is recrystallized from ethyl acetate to give 3-cyclopent-3-enyloxy-4-methoxybenzoic acid (1.31 g), in the form of a colorless solid, m.p. 171°-173° C. [Elemental analysis: C,66.6; H,6.0%; calculated: C,66.7; H,6.0%].

Workup

  1. customthe layers are separated
  2. extractionthe aqueous layer is extracted with t-butyl methyl ether (3×30 mL)
  3. washThe combined organic layers are washed with water (2×15 mL)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customThe resulting residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f42a61f46fc24d0aa66dc0ab993ef937
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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