Acetic Acid → 4'-Methoxy-4-(2-methylbutyl)biphenyl

HRID 231007Notes

Reaction equation

HRID 231007 reaction equation
Cl.C(O)(=O)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=O)[CH:21]([CH3:24])[CH2:22][CH3:23])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1>[Zn].[Hg]Cl.CCOCC.O.C1(C)C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([CH3:24])[CH2:22][CH3:23])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

9

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric Acid3×HCID 151139424'-Methoxy-4-(2-methylbutyryl)biphenyl

Product 1

HCID 117369194'-Methoxy-4-(2-methylbutyl)biphenylYield 74%

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 24182Mercurous ChlorideCatalystHCID 962WaterSolvent3×HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

13.6 g of zinc powder, 1.4 g of mercury chloride, 0.7 ml of conc. hydrochloric acid, and 20 ml of water were mixed with shaking for five minutes, and then the supernatant solution was flowed out. To the obtained zinc amalgam, 10 ml of water, 24 ml of conc. hydrochloric acid, 1 ml of acetic acid, 14 ml of toluene, and 38 m moles(10.2 g) of 4'-methoxy-4-(2-methylbutyryl)biphenyl were added, and then refluxed for 20 hours. In the mean time, 5 ml portions of conc. hydrochloric acid was successively added every five hours. The reaction solution was cooled to room temperature, then, after the addition of water, ether extracted. The extract was washed with water, dried, and concentrated, and then purified by column chromatography, to obtain 7.1 g of 4'-methoxy-4-(2-methylbutyl)biphenyl. (yield: 74%)

Workup

  1. temperaturerefluxed for 20 hours
  2. extractionextracted
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-691cfbe060bf459d9b6850de7d6a6d4e
Source dataset
uspto-grants-1989_07
Patent number
US04844835

Reaction notes

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