Nitric Acid → rac-(1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acid

HRID 922191Notes

Reaction equation

HRID 922191 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:13]([O-])([OH:15])=[O:14]>>[N+:13]([C:4]1[CH:5]=[CH:6][C:1]([C@@H:7]2[CH2:9][C@H:8]2[C:10]([OH:12])=[O:11])=[CH:2][CH:3]=1)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 237413trans-2-Phenylcyclopropanecarboxylic acid

Product 1

HCID 12854631rac-(1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acidYield 78.2%

Conditions

Temperature
0 °C

Procedure

To a 1000 mL RB flask fitted with magnetic stirrer was charged with 150 mL of HNO3, cooled to 0° C., was added (1R,2R)-2-phenylcyclopropanecarboxylic acid (15 g, 92.593 mmol) portion wise for half an hour, RM brought to RT and stirred for 3 h. After the completion of reaction, RM was poured into ice cold water, stirred for 30 min and filtered off the product and dried under vacuum. The obtained product was white color solid (15 g, yield: 78.2%).

Workup

  1. customTo a 1000 mL RB flask fitted with magnetic stirrer
  2. custombrought to RT
  3. customAfter the completion of reaction, RM
  4. additionwas poured into ice cold water
  5. stirringstirred for 30 min
  6. filtrationfiltered off the product
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0c716ac984c1436d89ea9ae77734585b
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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