4-Hydroxybenzoic Acid → 4-({6-[(3-Methyloxetan-3-yl)methoxy]hexyl}oxy)benzoic acid

HRID 2211570Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]1([CH3:14])[CH2:13][O:12][CH2:11]1.[OH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:14][C:10]1([CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:13][O:12][CH2:11]1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution comprising 20 g of 3-[(6-bromohexyloxy)methyl]-3-methyloxetane, 11.6 g of 4-hydroxybenzoic acid, 13 g of potassium carbonate and 150 ml of dimethylformamide was stirred at 90° C. for 4 hours. Water was added to the reaction liquid to terminate the reaction, and the liquid was extracted with ethyl acetate. The organic layer was washed with water, and the solvent was distilled off. A 5% sodium hydroxide aqueous solution was added to the resulting residue, and the solution was refluxed for 8 hours. Then, the solution was acidified with hydrochloric acid and extracted with ether, followed by drying on anhydrous magnesium sulfate. The solvent was distilled off to obtain 17 g of 4-[6-(3-methyloxetane-3-ylmethoxy)hexyloxy]benzoic acid. Melting point: 61° C.

Workup

customto terminate
customthe reaction
extractionthe liquid was extracted with ethyl acetate
washThe organic layer was washed with water
distillationthe solvent was distilled off
additionA 5% sodium hydroxide aqueous solution was added to the resulting residue
temperaturethe solution was refluxed for 8 hours
extractionextracted with ether
dry with materialby drying on anhydrous magnesium sulfate
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-0e5bed5ab06a47f682d42bb9a3f817e6
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101595B2

Reaction notes

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