Potassium Hydroxide → Acetic acid, (3-pentadecylphenoxy)-

HRID 2399222Notes

Reaction equation

HRID 2399222 reaction equation
[OH-].[K+].[CH2:3]([C:18]1[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=1)[O:21][CH2:22][C:23]([O:25]C)=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CO>[CH2:3]([C:18]1[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=1)[O:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54375866HCID 54375866, compound

Product 1

HCID 203275Acetic acid, (3-pentadecylphenoxy)-Yield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2-L round bottom flask equipped with a magnetic stirring bar and a reflux condenser was charged with potassium hydroxide (28 g, 0.5 mol) and methanol (1-L). To this vigorously stirred mixture, methyl (3-pentadecylphenoxy)acetate (93 g, 0.247 mol) was added and the resulting slurry was brought to a gentle reflux (2 hr). The ester was not completely soluble. The reaction was monitored by TLC. The hydrolysis was complete in 2 hr. The mixture was cooled and poured into crushed ice-water-hydrochloric acid mixture to precipitate the acid as white solid. The acid was dried and further purified by trituration from hot methanol to afford 82 g (92% yield) of the acid, mp 96° C.

Workup

  1. customA 2-L round bottom flask equipped with a magnetic stirring bar and a reflux condenser
  2. temperaturea gentle reflux (2 hr)
  3. temperatureThe mixture was cooled
  4. additionpoured
  5. customto precipitate the acid as white solid
  6. customThe acid was dried
  7. customfurther purified by trituration from hot methanol

Sources & evidence

ORD record
ord-5ce9e4ecd43b43109eb68be3153945ea
Source dataset
uspto-grants-1995_09
Patent number
US05447830

Reaction notes

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