3-Cyclopent-2-enyloxy-4-methoxybenzaldehyde → 3-Cyclopent-2-enyloxy-4-methoxybenzoic acid

HRID 1994327Notes

Reaction equation

HRID 1994327 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][CH2:4][CH:3]=[CH: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])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 221458283-Cyclopent-2-enyloxy-4-methoxybenzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 221456893-Cyclopent-2-enyloxy-4-methoxybenzoic acidYield 71.3%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 3-cyclopent-2-enyloxy-4-methoxybenzaldehyde (7.70 g) in t-butanol (160 mL) and 2-methyl-2-butene (40 mL) is treated dropwise with an aqueous solution (150 mL) containing sodium chlorite (80% technical grade; 4.39 g) and sodium dihydrogen phosphate (38.49 g), and left to stand overnight. The resulting mixture is extracted with dichloromethane (2×250 mL), and the combined organic layers are dried over sodium sulfate, the solvent is removed under reduced pressure, and the resulting residue is recrystallized from ethyl acetate, to give 3-cyclopent-2-enyloxy-4-methoxybenzoic acid (5.89 g), in the form of a colorless solid. m.p. 160-163° C. [Elemental analysis: C, 66.4; H, 6.0%. calculated: C, 66.7; H, 6.0%].

Workup

  1. waitleft
  2. extractionThe resulting mixture is extracted with dichloromethane (2×250 mL)
  3. dry with materialthe combined organic layers are dried over sodium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customthe resulting residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-948eb8efa29f4098b1075b25029e340e
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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