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

HRID 993276Notes

Reaction equation

HRID 993276 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 fromethyl 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 fromethyl acetate

Sources & evidence

ORD record
ord-d2c1fef5ae1b4d4394e6d4265cadfd18
Source dataset
uspto-grants-2002_10
Patent number
US06472412B1

Reaction notes

Loading…