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

HRID 746345Notes

Reaction equation

HRID 746345 reaction equation
[CH3:1][C:2]1([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=2)[CH2:5][O:4][CH2:3]1.[OH-].[Na+].Cl>O>[CH3:1][C:2]1([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:24][CH:25]=2)[CH2:5][O:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67067014HCID 67067014, compound

Product 1

HCID 219606224-({6-[(3-Methyloxetan-3-yl)methoxy]hexyl}oxy)benzoic acidYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4-[6-(3-methyloxetane-3-ylmethoxy)hexyloxy]benzoate (83 g), sodium hydroxide (12 g), water (50 mL), and Solmix (registered trademark: 200 ml) was refluxed for 2 hours. The reaction mixture was rendered acidic with hydrochloric acid, extracted with ethyl acetate and an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off to obtain 4-[6-(3-methyloxetane-3-ylmethoxy)hexyloxy)benzoic acid (OX1: 63 g). Melting point: 58.5° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialan organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-40a0cf407e4a4e41b1698b49583d8b59
Source dataset
uspto-grants-2008_07
Patent number
US07393569B2

Reaction notes

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