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

HRID 990632Notes

Reaction equation

HRID 990632 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 TLC (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-8148f61d8e924dcc9854f774ed9fc44e
Source dataset
uspto-grants-2002_10
Patent number
US06462034B1

Reaction notes

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