Hydrochloric Acid → HCID 68453552, compound

HRID 2353786Notes

Reaction equation

HRID 2353786 reaction equation
[CH2:1]([O:4][C:5]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:6]=1[C:7]([O:9]CCC)=[O:8])[CH2:2][CH3:3].CC(C)([O-])C.[K+].CCCCCC.C(OCC)(=O)C.Cl>CS(C)=O>[CH2:1]([O:4][C:5]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:6]=1[C:7]([OH:9])=[O:8])[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxideHCID 68452837HCID 68452837, compound

Product 1

HCID 68453552HCID 68453552, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of Propyl 2-propoxy-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-Propoxy-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-cae38c2614444c44b39b9c7819ef415c
Source dataset
uspto-grants-2010_07
Patent number
US07750047B2

Reaction notes

Loading…