Water → (2,4-Bis(1,1-dimethylpropyl)phenoxy)acetic acid

HRID 1756889Notes

Reaction equation

HRID 1756889 reaction equation
[C:1]([C:6]1[CH:18]=[C:17]([C:19]([CH2:22][CH3:23])([CH3:21])[CH3:20])[CH:16]=[CH:15][C:7]=1[O:8][CH2:9][C:10]([O:12]CC)=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2].[OH-].[Na+].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1>[C:1]([C:6]1[CH:18]=[C:17]([C:19]([CH2:22][CH3:23])([CH3:21])[CH3:20])[CH:16]=[CH:15][C:7]=1[O:8][CH2:9][C:10]([OH:12])=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 19391876Ethyl [2,4-bis(2-methylbutan-2-yl)phenoxy]acetate

Product 1

HCID 83411(2,4-Bis(1,1-dimethylpropyl)phenoxy)acetic acidYield 133.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The above ethyl 2-(2,4-di-t-amylphenoxy)acetate (293 g) and 27% aqueous sodium hydroxide (401.4 g) were placed in a 3-liter flask. The mixture was kept at 98° C. for 6 hours, and the hydrolysis reaction was completed. After completion of the reaction, the mixture was adjusted to pH 2 or lower by the addition of 40% aqueous sulfuric acid (349.9 g) and water (250 g), and toluene (289.5 g) was added thereto, followed by extraction. The water layer was separated with a separatory funnel, and the toluene layer was washed with water (289.5 g). Then, the toluene layer was concentrated by distillation under ordinary pressure for the recovery of toluene, which afforded a concentrated solution (357.6 g) of the carboxylic acid compound in toluene. The analysis revealed that the concentrated solution contained the desired carboxylic acid compound in a yield of 99% on the basis of the raw material ester compound.

Workup

  1. customthe hydrolysis reaction
  2. customAfter completion of the reaction
  3. additionwas added
  4. extractionfollowed by extraction
  5. customThe water layer was separated with a separatory funnel
  6. washthe toluene layer was washed with water (289.5 g)
  7. concentrationThen, the toluene layer was concentrated by distillation under ordinary pressure for the recovery of toluene, which

Sources & evidence

ORD record
ord-145f2852474d403f8ef98a103d0fb8c9
Source dataset
uspto-grants-1995_08
Patent number
US05442114

Reaction notes

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