Hydrochloric Acid → 2-Ethoxy-6-pentadecylbenzoic Acid

HRID 2353810Notes

Reaction equation

HRID 2353810 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:5]=1[C:6]([O:8]CC)=[O:7])[CH3:2].CC(C)([O-])C.[K+].CCCCCC.C(OCC)(=O)C.Cl>CS(C)=O>[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:5]=1[C:6]([OH:8])=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 22574569Ethyl 2-Ethoxy-6-pentadecylbenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 684514982-Ethoxy-6-pentadecylbenzoic AcidYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
68 °C

Procedure

To a stirred solution of Ethyl 2-Ethoxy-6-pentadecylbenzoate (20 g, 240 mmol) in dimethyl sulfoxide (80 mL) was added potassium tert-butoxide (20 g, 890 mmol) in portions. The solution was heated to 68° C. on a water bath for 3 h, the reaction was monitored by TLC using a hexane-ethyl acetate (9:1) solvent system. The reaction mass was cooled to 15° C., poured into ice water, and then acidified with 10% dilute hydrochloric acid. The precipitated solid was filtered and washed thoroughly with distilled water, and the crude mass was recrystallized in petroleum ether (50 mL) to yield an off-white solid of 2-Ethoxy-6-pentadecylbenzoic Acid (15 g, 80%).

Workup

  1. temperatureThe reaction mass was cooled to 15° C.
  2. filtrationThe precipitated solid was filtered
  3. washwashed thoroughly with distilled water
  4. customthe crude mass was recrystallized in petroleum ether (50 mL)

Sources & evidence

ORD record
ord-3acf54f8bd334969bbb9c37625d65c12
Source dataset
uspto-grants-2010_07
Patent number
US07750047B2

Reaction notes

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