ChemicalBook CAS DataBase List (-)-Corey lactone 4-phenylbenzoate alcohol

(-)-Corey lactone 4-phenylbenzoate alcohol synthesis

7synthesis methods

Product Name:(-)-Corey lactone 4-phenylbenzoate alcohol
CAS Number:31752-99-5
Molecular formula:C21H20O5
Molecular Weight:352.38

32233-40-2 Synthesis

32233-40-2
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$9.00/250mg

14002-51-8 Synthesis

14002-51-8
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$21.00/1g

(-)-Corey lactone 4-phenylbenzoate alcohol

31752-99-5
247 suppliers
$19.00/250mg

Yield:31752-99-5 93.45%

Reaction Conditions:

Stage #1: (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-onewith pyridine;trityl chloride at 20; for 12 h;Large scale;
Stage #2: 4-biphenyl-carboxylic acid chloride at 30; for 4.5 h;Large scale;Temperature;

Steps:

14 Example 14: One Pot Preparation of (-)-corey lactone

Into a reaction vessel with a filter element at the bottom, 40 L of pyridine was added, and (-) Cretocene diol 4 kg (1 eq) was added under stirring, and 6.48 kg (1 eq) of triphenylchloromethane was added.The temperature was controlled at 20 °C for 12h to complete the reaction. 5.54kg (1.1eq) of biphenyl-4-formyl chloride was added. The temperature was controlled at 30 °C for 4.5h to complete the reaction.40L of pure water was added to the reaction vessel and stirred for 2 hours to obtain a suspension. Nitrogen gas was introduced into the reaction vessel, and the suspension was filtered through a filter element.Ethanol 40L was added to the reaction vessel, and the mixture was heated to reflux for 1 hour. The liquid was pressure filtered to obtain a solid powder.60L of tetrahydrofuran was added to the reaction vessel, 30L (4mol/L) hydrochloric acid aqueous solution was added dropwise, and the reaction was completed at a temperature of 45° C. for 3.5 h to complete reaction. The reaction system was cooled to 10° C., and saturated aqueous sodium carbonate was added to neutralize the reaction to PH=7.;The solvent in the reactor was evaporated under reduced pressure and the crude product was obtained by pressure filtration.50L of n-propyl ether was added to the reaction vessel, and the mixture was heated to reflux for 3 hours, and then dried by pressure filtration to give the product (-)biphenyl-4-formyl-colyactone 7.66 kg. The yield was 93.45%, and the purity was 99.41%.

References:

CN108033937,2018,A Location in patent:Paragraph 0113; 0117; 0127; 0131; 0136; 0137; 0143