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

HRID 1593915Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]1([CH2:14][CH3:15])[CH2:13][O:12][CH2:11]1.[OH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:14]([C:10]1([CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=2)[CH2:13][O:12][CH2:11]1)[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

First stage: A solution prepared by dissolving 500 g of 3-[(6-bromohexyloxy)methyl]-3-ethyloxetane, 297 g of 4-hydoxybenzoic acid and 490 g of potassium carbonate in 3 L of dimethylforamide was stirred at 90° C. for 8 hours. After adding 4 L of water to the reaction mixture, it was extracted with 4 L of toluene. The organic layer was washed with water, and then the solvent was distilled off. Added to the resulting residue were 200 g of sodium hydroxide, 1 L of water and 2.5 L of ethanol, and the mixture was refluxed for 4 hours. Ethanol 1 L was distilled off at an atmospheric pressure, and then the solution was acidified by hydrochloric acid to obtain a slurry. The slurry was filtered and dried to thereby obtain 400 g of 4-[6-(3-ethyloxetane-3-ylmethoxy) hexyloxy]benzoic acid (melting point: 58.5° C.).

Workup

customFirst stage: A solution prepared
extractionwas extracted with 4 L of toluene
washThe organic layer was washed with water
distillationthe solvent was distilled off
additionAdded to the resulting residue
temperaturethe mixture was refluxed for 4 hours
distillationEthanol 1 L was distilled off at an atmospheric pressure
customto obtain a slurry
filtrationThe slurry was filtered
customdried

Sources & evidence

ORD record: ord-5958c7f071e84ed7af3ac059efc2ff9c
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07300604B2

Reaction notes

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