Ethylene Glycol → 1-(4-Bromophenyl)cyclobutane-1-carboxylic acid

HRID 2104128Notes

Reaction equation

HRID 2104128 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]#N)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:14].[K+].C(O)C[OH:18].Cl>CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([OH:18])=[O:14])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 201116081-(4-Bromophenyl)cyclobutanecarbonitrile

Product 1

HCID 167699191-(4-Bromophenyl)cyclobutane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-bromophenyl)cyclobutanecarbonitrile (1-2c, 12.04 g, 51.0 mmol), potassium hydroxide (11.44 g, 204 mmol) and ethylene glycol (50 mL, 897 mmol) were heated to reflux for 4 h. The reaction mixture was cooled to room temperature, then diluted with EtOAc and water. The aqueous layer was acidified with 1 M HCl, then was extracted into EtOAc. The organic layer was dried over Na2SO4, filtered and reduced in vacuo to give 7-1 as a tan oil.

Workup

  1. temperatureto reflux for 4 h
  2. extractionwas extracted into EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-fec0401626aa44378b11926f24cda9ef
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

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