p-Toluenesulfonic acid → HCID 137331261, compound

HRID 1587265Notes

Reaction equation

HRID 1587265 reaction equation
OC1C=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=CC=1.[CH2:17]([Si:21](C)(C)CCCO)[CH2:18][CH2:19][CH3:20].[C:28]1([CH3:38])[CH:33]=[CH:32][C:31](S(O)(=O)=O)=[CH:30][CH:29]=1.[C:39]1([CH3:46])C(C)=CC=CC=1.C(OCC)(=[O:49])C>>[CH2:13]([C:12]1[C:20]([CH2:19][CH2:18][CH2:17][SiH3:21])=[C:38]([C:28]2[CH:33]=[CH:32][C:31]([OH:49])=[CH:30][CH:29]=2)[C:39]([CH3:46])=[C:10]([CH3:9])[C:11]=1[C:14]([OH:16])=[O:15])[CH2:8][CH2:5][CH3:6]

Participants

6

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 7237O-Xylene2×HCID 8857Ethyl AcetateHCID 3015564'-Hydroxy-4-biphenylcarboxylic acidHCID 197575723-[Butyl(dimethyl)silyl]propan-1-ol

Product 1

HCID 137331261HCID 137331261, compoundYield 47.6%

Procedure

2.27 g (10.6 mM) of 4-hydroxybiphenyl-4'-carboxylic acid, 3.71 g (21.3 mM) of butyldimethyl-3-hydroxypropylsilane, 0.25 g (1.31 mM) of p-toluenesulfonic acid and 30 ml of xylene were mixed and heat-refluxed for 8 hours under stirring. After the reaction, the reaction mixture was cooled, followed by distilling-off of xylene under reduced pressure. The resultant residue was dissolved in ethyl acetate and washed with water, followed by drying with anhydrous magnesium sulfate. The magnesium sulfate in the resultant mixture was filtered off and the filtrate was condensed into a solid under reduced pressure, followed by purification by silica gel column chromatography (eluent: toluene) to obtain 1.87 g of 3-butyldimethyl-silylpropyl 4'-hydroxybiphenyl-4-carboxylic acid (Yield; 47.6 %).

Workup

  1. temperatureheat-refluxed for 8 hours
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled
  4. washwashed with water
  5. dry with materialby drying with anhydrous magnesium sulfate
  6. filtrationThe magnesium sulfate in the resultant mixture was filtered off
  7. customcondensed into a solid under reduced pressure
  8. customfollowed by purification by silica gel column chromatography (eluent: toluene)

Sources & evidence

ORD record
ord-9da45bf192ad4e2e93319a64d3d301a6
Source dataset
uspto-grants-1993_06
Patent number
US05217645

Reaction notes

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