Methyl chloroacetate → HCID 59253951, compound

HRID 83811

Reaction equation

HRID 83811 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 of (4-nitrophenoxy)acetic acid 22 (150 g, 761.4 mmol) and triethyl-amine (85 g, 840 mmol) in acetone (750 ml) was added methyl chloroacetate (91.6 g, 844 mmol) drop wise and stirred under reflux for 8 hours. Solids were filtered off and poured onto cold 5% sodium bicarbonate solution (4 L). Crude 44 was filtered, dried and recrystallised from chloroform:hexane (1:6) to get pure 44 (186 g, 90.8%) as a white powder with an m.p. between 88-90° C.

Workup

  1. temperatureunder reflux for 8 hours
  2. filtrationSolids were filtered off
  3. additionpoured onto cold 5% sodium bicarbonate solution (4 L)
  4. filtrationCrude 44 was filtered
  5. customdried
  6. customrecrystallised from chloroform:hexane (1:6)

Sources & evidence

ORD record
ord-d17d530434914752a853376796162732
Source dataset
uspto-grants-2014_09
Patent number
US08846845B2

Linked notes

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