Acetic Anhydride → 144728-22-3

HRID 1503075Notes

Reaction equation

HRID 1503075 reaction equation
[C:1]([CH2:4][C:5]1([CH2:8][C:9]([OH:11])=[O:10])[CH2:7][CH2:6]1)([OH:3])=O.C(OC(=O)C)(=O)C>C1(C)C=C(C)C=C(C)C=1>[CH2:6]1[C:5]2([CH2:8][C:9](=[O:10])[O:11][C:1](=[O:3])[CH2:4]2)[CH2:7]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 125309912,2'-(Cyclopropane-1,1-diyl)diacetic acid

Product 1

HCID 54153109144728-22-3

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Conditions

Temperature
100 °C

Procedure

350 g crude (1-carboxymethyl-cyclopropyl)-acetic acid (2.2 mole, 92% purity, from step 1) are suspended in a mixture of 350 ml of mesitylene and 678 g of acetic anhydride (6.6 mole, 3 eq) and heated to 100° C. Upon reaching that temperature, the pressure is reduced to approximately 200 mbar and 45% of the solvent mixture are distilled off (distillation takes approx. 1 h). Then the mixture is slowly cooled to 0-5° C. and the precipitate is collected by filtration. The filter cake is washed with 87 ml of cold mesitylene and then dried in vaccuo at 40° C.

Workup

  1. distillationare distilled off
  2. distillation(distillation takes approx. 1 h)
  3. temperatureThen the mixture is slowly cooled to 0-5° C.
  4. filtrationthe precipitate is collected by filtration
  5. washThe filter cake is washed with 87 ml of cold mesitylene
  6. customdried in vaccuo at 40° C.

Sources & evidence

ORD record
ord-8bb45a0a82fb4c56a3dd30f81ced4e0b
Source dataset
uspto-grants-2015_12
Patent number
US09212120B2

Reaction notes

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