Acetic Acid → 1-(2,6-dimethoxyphenyl)Cyclopropanecarboxylic acid

HRID 907465Notes

Reaction equation

HRID 907465 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:11]1([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12]1.[OH-].[Na+].[NH4+].[Cl-].CC(O)=O>C1COCC1.CO.O>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[C:11]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 57659403Ethyl 1-(2,6-dimethoxyphenyl)cyclopropanecarboxylate

Product 1

HCID 442449981-(2,6-dimethoxyphenyl)Cyclopropanecarboxylic acidYield 91.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture containing the ester 18 (21.11 g, 89.4 mmol) and 10 M NaOH (36 ml, 4 equiv) in THF (220 ml), MeOH (110 ml) and water (55 ml) was stirred at reflux for 4 days. Half-saturated NH4Cl (600 ml) and AcOH (25 ml) were then added and the acid 19 was extracted into i-PrOAc. The organics were dried over Na2SO4 and concentrated. Trituration of the residue in ether:hexane 1:3 (200 ml) yielded 18.15 g (91%) of 19 as a white solid.

Workup

  1. temperatureat reflux for 4 days
  2. extractionthe acid 19 was extracted into i-PrOAc
  3. dry with materialThe organics were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3aa1f1043e5b496a8876aec4d187a584
Source dataset
uspto-grants-2011_09
Patent number
US08013159B2

Reaction notes

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