Methyl chloroacetate → HCID 59253951, compound

HRID 1882328Notes

Reaction equation

HRID 1882328 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.Cl[CH2:23][C:24]([O:26][CH3:27])=[O:25]>CC(C)=O>[CH3:27][O:26][C:24]([CH2:23][O:11][C:10](=[O:12])[CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=1)=[O:25]

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 8471TriethylamineHCID 15720(4-Nitrophenoxy)acetic acid

Product 1

HCID 59253951HCID 59253951, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture (4-Nitrophenoxy)acetic acid 94 (150 grams, 761.4 mmol), Triethylamine (85 grams, 840 mmol) in acetone (750 mL) was added methyl chloroacetate (91.6 grams, 844 mmol) drop wise, later stirred under reflux for 8 hours. Solids were filtered off and poured on to cold 5% sodium bicarbonate solution (4 lit). Crude 95 was filtered, dried, and recrystallized from chloroform:hexane (1:6) to get pure 95 (186 grams, 90.8%) as a white powder. M.p: 88-90° C. IH NMR (CDCl3) δ 3.80 (s, 3H, Ester), 4.75 (s, 2H, OCH2), 4.88 (s, 2H, OCH2), 7.02 (d, 2H, Ar), 8.22 (d, 2H, Ar).

Workup

  1. temperatureunder reflux for 8 hours
  2. filtrationSolids were filtered off
  3. additionpoured on to cold 5% sodium bicarbonate solution (4 lit)
  4. filtrationCrude 95 was filtered
  5. customdried
  6. customrecrystallized from chloroform:hexane (1:6)

Sources & evidence

ORD record
ord-1505eb49383f4c7fa81be03c172a5205
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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