ChemicalBook CAS DataBase List 4,4'-DI-TERT-BUTYLDIPHENYLMETHANE

4,4'-DI-TERT-BUTYLDIPHENYLMETHANE synthesis

10synthesis methods

Product Name:4,4'-DI-TERT-BUTYLDIPHENYLMETHANE
CAS Number:19099-48-0
Molecular formula:C21H28
Molecular Weight:280.45

507-20-0 Synthesis

507-20-0
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101-81-5
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19099-48-0
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$57.79/10g

Yield: 74%

Reaction Conditions:

aluminum (III) chloride at 20;Product distribution / selectivity;

Steps:

1
Examples Example 1 Preparation of 4,4'-Di-tert-butyldiphenylmethane.; [Show Image] In a 500-ml flask, to a mixture of 16.8 g (100 mmol) of diphenylmethane and 21.3 g (230 mmol) of tert-butyl chloride, 67 mg (0.5 mmol) of anhydrous AlCl₃ were added, at room temperature, under vigorous stirring, resulting in immediate HCl gas emission. The reaction mixture turned red. After 5 min, a second portion of 67 mg (0.5 mmol) of AlCl₃ were added. After 5 min of vigorous stirring, the reaction mixture became hard. After about 1 h, the hard mass obtained was recrystallised from about 100 mL of hot isopropanol. The crystalline product precipitated from this solution at a temperature of -30 °C after a period of time of about 2 to 3 h. It was separated, washed with 50 ml of cold isopropanol, and dried in vacuum under a reduced pressure of 10 to 20 mm Hg. 19.6 g of product were obtained with a yield of 70%. The procedure was repeated with a yield ranging between 67 and 74%. Anal. for C₂₁H₂₈: Calculated: C 89.94, H 10.06. Found: C 89.86, H 10.03. ¹H NMR (CDCl₃): δ 7.31 (d, J=8.4 Hz, 4H), 7.13 d, J=8.4 Hz, 4H), 3.92 (s, 2H), 1.30 (s, 18H). ¹³C{¹H} NMR (CDCl₃): δ 148.7, 138.2, 128.5, 125.2, 41.0, 34.3, 31.4.

References:

TOTAL PETROCHEMICALS RESEARCH FELUY EP1999091, 2010, B1 Location in patent:Page/Page column 4

101-81-5
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128-37-0 Synthesis