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Chemical Structure| 35468-69-0 Chemical Structure| 35468-69-0

Structure of 35468-69-0

Chemical Structure| 35468-69-0

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Product Details of [ 35468-69-0 ]

CAS No. :35468-69-0
Formula : C10H12O3
M.W : 180.20
SMILES Code : CCC(C1=CC=CC=C1)(O)C(O)=O
MDL No. :MFCD00109290

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Application In Synthesis of [ 35468-69-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 35468-69-0 ]

[ 35468-69-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 35468-69-0 ]
  • [ 677-22-5 ]
  • [ 80565-30-6 ]
  • 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylbutyric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; p-toluenesulfonic acid monohydrate; In tetrahydrofuran; water; chlorobenzene; EXAMPLE 10 A mixture of 4-(4-chlorophenyl)benzaldehyde (20.3 g.), 2-hydroxy-2-phenylbutyric acid (20.4 g.) and p-toluenesulphonic acid monohydrate (1.5 g.) was heated in chlorobenzene (180 ml.) at reduced pressure (160 mm. Hg) under reflux for four hours and with continuous removal of water by azeotropic distillation. The mixture was then cooled, added to water (120 ml.) and the pH of the aqueous phase adjusted to 7 to 8 with caustic soda liquor. The chlorobenzene was removed by azeotropic distillation with water and the resulting aqueous mixture was extracted with 100-120 petrol (260 ml.) at 80 C. After washing with water, the organic phase was dried by azeotropic distillation to give a suspension of 2-[4-(4-chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-one. To this suspension was added a solution of t-butyl magnesium chloride (35.2 g., estimated by compleximetric titration) in tetrahydrofuran (180 ml.) during 60 minutes. During this period the temperature was kept at 18 to 20 C. After stirring the suspension for a further 2 hours, dilute hydrochloric acid [prepared from concentrated hydrochloric acid (25 ml.) and water (50 ml.)] was added maintaining the temperature below 30 C. The organic phase was separated, washed with water (2*50 ml.) and then treated as described in Example 9. There was thus obtained 2-[4-(4-chlorophenyl)benzyloxy]-2-phenylbutyric acid (14.2 g.), m.p. 128-130 C. (after recrystallisation from ethylbenzene).
  • 2
  • [ 35468-69-0 ]
  • [ 80565-30-6 ]
  • [ 80565-32-8 ]
YieldReaction ConditionsOperation in experiment
With p-toluenesulfonic acid monohydrate; In cyclohexane; EXAMPLE 6 A mixture of 4-(4-chlorophenyl)benzaldehyde (8.7 g.), 2-hydroxy-2-phenylbutyric acid (8.6 g.) and p-toluenesulphonic acid monohydrate (0.76 g.) was heated in cyclohexane (160 ml.) under reflux for 3 hours with continuous removal of water by azeotropic distillation. The mixture was then cooled, diluted with ethyl acetate (20 ml.) and washed with 10% w/v potassium carbonate solution (3*50 ml.) and then with water (2*50 ml.). The solution was dried (Na2 SO4), filtered, evaporated and triturated with methanol to give 2-[4-(4-chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-one (14.7 g.), m.p. 80-83 C. (after recrystallisation from methanol).
With trifluoroborane diethyl ether; In diethyl ether; EXAMPLE 7 To a stirred solution of 4-(4-chlorophenyl)benzaldehyde (2.16 g.) and 2-hydroxy-2-phenylbutyric acid (1.8 g.) in anhydrous diethyl ether (50 ml.) was added boron trifluoride etherate (2.2 g.). After stirring at room temperature for 12 hours, the solution was washed with 10% w/v sodium acetate solution (2*20 ml.) and then with water (2*20 ml.) and dried (Na2 SO4). The solution was filtered and evaporated to give an oil which on crystallisation from methanol gave 2-[4-(4-chlorophenyl)phenyl]-5-ethyl-5-phenyl-1,3-dioxolan-4-one (1.7 g.) m.p. 80-83 C.
 

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