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

HRID 130272Notes

Reaction equation

HRID 130272 reaction equation
CN(C)C=O.Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][C:15]1([CH2:19][CH3:20])[CH2:18][O:17][CH2:16]1.[OH:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:19]([C:15]1([CH2:14][O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][O:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)[CH2:18][O:17][CH2:16]1)[CH3:20]

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 592073103-{[(6-Bromohexyl)oxy]methyl}-3-ethyloxetane

Product 1

HCID 597675964-({6-[(3-Ethyloxetan-3-YL)methoxy]hexyl}oxy)benzoic acidYield 66.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dimethylformamide (3 L) solution of 3-[(6-bromohexyloxy)methyl]-3-ethyloxetane 500 g, 4-hydroxybenzoic acid 297 g and potassium carbonate 490 g was stirred at 90° C. for 8 hours. Water 4 L was added to the reaction mixture, and then it was extracted with toluene 4 L. The organic layer was washed with water, and the solvent was distilled off. Sodium hydroxide 200 g, water 1 L and ethanol 2.5 L were added to the resulting residue and refluxed for 4 hours. Ethanol (1 L) was distilled off at 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

  1. extractionit was extracted with toluene 4 L
  2. washThe organic layer was washed with water
  3. distillationthe solvent was distilled off
  4. additionSodium hydroxide 200 g, water 1 L and ethanol 2.5 L were added to the resulting residue
  5. temperaturerefluxed for 4 hours
  6. distillationEthanol (1 L) was distilled off at atmospheric pressure
  7. customto obtain a slurry
  8. filtrationThe slurry was filtered
  9. customdried

Sources & evidence

ORD record
ord-2a05641a385e4dafafa03acb0082da18
Source dataset
uspto-grants-2008_06
Patent number
US07381350B2

Reaction notes

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