18-Crown-6 → HCID 53845706, compound

HRID 2121143Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1OCCOCCOCCOCCOCCOC1.[N:38]1[CH:43]=[CH:42][CH:41]=[C:40]([O:44]C2C=NC=CC=2)[CH:39]=1.[K]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:44][C:40]2[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=2)=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution in toluene (25 mL) of 4-bromomethyl-2-phenoxybenzoic acid methyl ester (3.37 g), prepared as in Example 157E, was added 18-crown-6 (0.52 g) and the potassium 3-pyridyloxide (2.20 g). The reaction mixture was heated at 70° C. for 1 hour during which time a black, insoluble tar formed. The reaction mixture was cooled to ambient temperature and diluted with toluene. The toluene was decanted from the tar and the tar was dissolved in 1:1 THF-water (20 mL). The aqueous THF was added to the toluene and the mixture was washed twice with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give a black oil. Chromatography on silica gel (1:1 ethyl acetate-hexanes) gave 4-(3-pyridyloxymethyl)-2-phenoxybenzoic acid methyl ester (2.47 g).

Workup

customformed
temperatureThe reaction mixture was cooled to ambient temperature
customThe toluene was decanted from the tar
dissolutionthe tar was dissolved in 1:1 THF-water (20 mL)
additionThe aqueous THF was added to the toluene
washthe mixture was washed twice with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a black oil

Sources & evidence

ORD record: ord-ad444eb570ec46ca8865252666baca82
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06693123B2

Reaction notes

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