Potassium Carbonate → Methyl 4-cyclohex-1-en-1-yl-2-[(4'-methoxy-1,1'-biphenyl-4-yl)oxy]butanoate

HRID 559071

Reaction equation

HRID 559071 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Cl[CH:23]([CH2:28][CH2:29][C:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=1)[C:24]([O:26][CH3:27])=[O:25]>CC(CC)C(=O)C>[C:30]1([CH2:29][CH2:28][CH:23]([O:21][C:18]2[CH:17]=[CH:16][C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=3)=[CH:20][CH:19]=2)[C:24]([O:26][CH3:27])=[O:25])[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110308394-Hydroxy-4'-methoxybiphenylHCID 24973934Methyl 2-chloro-4-cyclohex-1-en-1-ylbutanoate

Product 1

HCID 66998883Methyl 4-cyclohex-1-en-1-yl-2-[(4'-methoxy-1,1'-biphenyl-4-yl)oxy]butanoate

Reagents, catalysts & solvents 1

HCID 112623-Methylpentan-2-OneSolvent2×

Procedure

1.9 g (0.0138 mol) of potassium carbonate are added to a solution of 1.4 g (0.0069 mol) of 4′-methoxy-1,1′-biphenyl-4-ol in 30 ml of 3-methyl-2-pentanone (MIBK). The mixture is refluxed for 30 minutes and a solution of 1.5 g (0.0069 mol) of methyl 2-chloro-4-cyclohex-1-en-1-ylbutanoate in 10 ml of 3-methyl-2-pentanone is then added. Refluxing is continued for a further 6 hours. After cooling to room temperature, the reaction medium is concentrated, taken up in water and extracted with ethyl acetate. The extracts are washed with 1N sodium hydroxide and then with saturated aqueous NaCl solution, and dried over Na2SO4. After concentrating, a thick oil is obtained, which is purified by flash chromatography (95/5 heptane/ethyl acetate) 1.1 g of an oily product are thus obtained.

Workup

  1. temperatureThe mixture is refluxed for 30 minutes
  2. temperatureRefluxing
  3. concentrationthe reaction medium is concentrated
  4. extractionextracted with ethyl acetate
  5. washThe extracts are washed with 1N sodium hydroxide
  6. dry with materialwith saturated aqueous NaCl solution, and dried over Na2SO4
  7. concentrationAfter concentrating
  8. customa thick oil is obtained
  9. customwhich is purified by flash chromatography (95/5 heptane/ethyl acetate) 1.1 g of an oily product
  10. customare thus obtained

Sources & evidence

ORD record
ord-2ddc9aa12c0240289199c1f8ac7f2d94
Source dataset
uspto-grants-2011_11
Patent number
US08063067B2

Linked notes

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