Triethylamine → 2-Chloro-4-methylphenyl 2,2-dimethylpropanoate

HRID 2292661Notes

Reaction equation

HRID 2292661 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>O1CCCC1>[CH3:19][C:18]([CH3:21])([CH3:20])[C:17]([O:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[Cl:1])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 148512-Chloro-4-methylphenolHCID 62493Pivaloyl chloride

Product 1

HCID 218336712-Chloro-4-methylphenyl 2,2-dimethylpropanoateYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-chloro-4-methylphenol (100 g), triethylamine (92.3 g) and anhydrous tetrahydrofuran (1 liter) was added dropwise pivalic chloride (93.0 g) at 5° to 10° C. under stirring over 1 hour. Then, after stirring at the same temperature for 3 hours, the reaction mixture was poured into ice water, which was extracted with diethyl ether. The organic layer was washed with 3% aqueous hydrochloric acid solution and then water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting oil was distilled under reduced pressure, which afforded 155.3 g of 2-chloro-4-methylphenyl 2,2-dimethylpropanoate as a colorless clear liquid. Yield, 97.7%.

Workup

  1. stirringThen, after stirring at the same temperature for 3 hours
  2. extractionwas extracted with diethyl ether
  3. washThe organic layer was washed with 3% aqueous hydrochloric acid solution
  4. dry with materialwater, dried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. distillationThe resulting oil was distilled under reduced pressure, which

Sources & evidence

ORD record
ord-f04cdcf9a93a4b5580a1a61ce2b4ee52
Source dataset
uspto-grants-1997_11
Patent number
US05684022

Reaction notes

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