Hydrochloric Acid → 2-Methoxy-6-pentadecylbenzoic acid

HRID 2055887Notes

Reaction equation

HRID 2055887 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:4]=1[C:5]([O:7]C)=[O:6].CC(C)([O-])C.[K+].CCCCCC.C(OCC)(=O)C.Cl>CS(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 313884Methyl 2-methoxy-6-pentadecylbenzoateHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 3138852-Methoxy-6-pentadecylbenzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of Methyl 2-methoxy-6-pentadecylbenzoate (10 g, 240 mmol) in dimethyl sulfoxide (40 mL) was added potassium tert-butoxide (10 g, 890 mmol) in portions. The solution was heated to 70° C. on a water bath for 2 h, and the progress of the reaction was monitored by TLC using a hexane-ethyl acetate (8:2) solvent system. The reaction mass was cooled to 10° C., poured into ice water, and then acidified with 5% dilute hydrochloric acid. The precipitated solid was filtered and washed thoroughly with distilled water, and the crude mass was recrystallized in hexane (50 mL) to yield an off-white solid of 2-Methoxy-6-pentadecylbenzoic Acid (7.6 g, 80%).

Workup

  1. temperatureThe reaction mass was cooled to 10° C.
  2. filtrationThe precipitated solid was filtered
  3. washwashed thoroughly with distilled water
  4. customthe crude mass was recrystallized in hexane (50 mL)

Sources & evidence

ORD record
ord-ecd2e11495c4453eaf9e34603d543ad7
Source dataset
uspto-grants-2008_02
Patent number
US07332629B2

Reaction notes

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