Methyl chloroacetate → (4-Nitrophenoxy)-acetic acid methoxycarbonylmethyl ester

HRID 501859Notes

Reaction equation

HRID 501859 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 59253951(4-Nitrophenoxy)-acetic acid methoxycarbonylmethyl esterYield 90.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of (4-nitrophenoxy) acetic acid 22 (150 g, 761.4 mmol) and triethylamine (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-d2b7e02f03ed425ab5114f16f0bbac25
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Reaction notes

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