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

HRID 2217106Notes

Reaction equation

HRID 2217106 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 reaction mixture comprising 83 g of ethyl 4-[6-(3-methyloxetan-3-ylmethoxy)hexyloxy]benzoate, 12 g of sodium hydroxide, 50 ml of water and 200 ml of Solmix (registered trade mark) was refluxed for 2 hours. This was made acidic with hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated away, and 63 g of 4-[6-(3-methyloxetan-3-ylmethoxy)hexyloxy]benzoic acid (OX1) was obtained. m.p.: 58.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. customThe solvent was evaporated away

Sources & evidence

ORD record
ord-1ca6b08c2acf4736b0945aaf9fb7911c
Source dataset
uspto-grants-2008_08
Patent number
US07407691B2

Reaction notes

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