Chloroacetyl chloride → Chloro-acetic acid 2,6-dimethyl-phenyl ester

HRID 1369302Notes

Reaction equation

HRID 1369302 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].C(NCCNC(C)C)(C)C.[Cl:20][CH2:21][C:22](Cl)=[O:23].CCOC(C)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][C:22](=[O:23])[CH2:21][Cl:20]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8857Ethyl AcetateHCID 113352,6-DimethylphenolHCID 77628N,N'-Diisopropylethylenediamine

Product 1

HCID 54160838Chloro-acetic acid 2,6-dimethyl-phenyl esterYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere: 2,6-dimethylphenol (1.0 equivalent, 40 mmoles) was dissolved in dichloromethane (40 mL) and diisopropyl ethylene diamine (1.3 equivalents, 53.2 mmoles). This solution was cooled to −78° C. Chloroacetylchloride was added all at once. The reaction was followed by 1TLC (25 EtOAc:75 Hexanes) until reaction was complete (˜10 minutes). The reaction was extracted using water and ether. The ether layer was washed with water and then brine, dried (MgSO4), filtered, rinsed with ether, and concentrated under vacuum. The concentrate was purified by silica gel column chromatography using hexanes as eluant, to afford 10.5 grams (94.6% yield) of chloro-acetic acid 2,6-dimethyl-phenyl ester product as a tan oil.

Workup

  1. custom(˜10 minutes)
  2. extractionThe reaction was extracted
  3. washThe ether layer was washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. filtrationfiltered
  6. washrinsed with ether
  7. concentrationconcentrated under vacuum
  8. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e698331a6cbb4d268e0f1474627f11f1
Source dataset
uspto-grants-2003_06
Patent number
US06576791B1

Reaction notes

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