Benzene → 2-(Dibenzofuran-4-ylthio)acetic acid

HRID 1029766Notes

Reaction equation

HRID 1029766 reaction equation
C[C:2]([CH3:11])([CH3:10])[C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4].CC(C)([CH2:16][OH:17])CO.C1(C)C=CC(S(O)(=O)=[O:26])=CC=1.[CH:30]1C=[CH:34][CH:33]=[CH:32][CH:31]=1>CCOCC>[CH:10]1[C:2]2[C:11]3[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=3[O:4][C:3]=2[C:5]([S:6][CH2:7][C:16]([OH:17])=[O:26])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 31344Neopentyl glycolHCID 27769762,2-Dimethyl-1-(thiophen-2-yl)propan-1-one

Product 1

HCID 199008292-(Dibenzofuran-4-ylthio)acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(2,2-dimethylpropionyl)thiophene (21.45 g), 2,2-dimethylpropane-1,3-diol (14.63 g), and a catalytic amount of p-toluenesulphonic acid in benzene (100 ml) was heated at reflux for 44 hours using a Dean and Stark apparatus. The mixture was cooled, diluted with ether (150 ml), and washed with saturated aqueous sodium hydrogen carbonate solution. The organic phase was then dried (MgSO4) and decolourised with activated charcoal. The solvent was removed by evaporation to give 2-t-butyl-5,5-dimethyl-2-(thien-2-yl)-1,3-dioxane (B) as a white solid (31.9 g, 98% yield); NMR: 0.57(s, 3H), 1.0(s, 9H), 1.21(s, 3H), 3.36(m, 2H), 3.62(d, 2H), 6.9(dd, 1H), 7.01(dd, 1H), 7.3(dd, 1H); mass spectrum (chemical ionisation) 255 (M+H)+.

Workup

  1. temperatureat reflux for 44 hours
  2. temperatureThe mixture was cooled
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialThe organic phase was then dried (MgSO4)
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-5bbcd6d4032f44a6a3ad581a13e38442
Source dataset
uspto-grants-1992_04
Patent number
US05102905

Reaction notes

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