65817-25-6

Upstream product

• 76650-22-1 (+/-)-2,3-dihydro-3β,5-dimethylbenzofuran-2β-ol 
• 76650-22-1 (+/-)-2,3-dihydro-3α,5-dimethylbenzofuran-2β-ol 
• 73444-58-3 2-methyl-2-(2'-acetoxy-4'-methylphenyl)-oxirane 
• 106-44-5 p-cresol 
• 600-22-6 pyruvic acid methyl ester 
• 85908-43-6 chloro-2 phenylthio-2 propionate de methyle 

Downstream Products

• 131516-82-0 2-(2-hydroxy-5-methyl-phenyl)-1-phenyl-propan-1-one 
• 1531624-30-2 (R)-phenyl 3,5-dimethyl-2-oxo-2,3-dihydrobenzofuran-3-carboxylate 
• 76650-25-4 2-(2'-Methoxy-5'-methylphenyl)-propanoic acid 

Relevant academic research and scientific papers

Direct enantioselective: C -acylation for the construction of a quaternary stereocenter catalyzed by a chiral bicyclic imidazole

A direct enantioselective C-acylation of 3-substituted benzofuran-2(3H)-ones (with up to 97% ee) was developed using a chiral bicyclic imidazole catalyst OAc-DPI and an achiral tertiary amine additive DIPEA. The reaction mechanism for the direct C-acylation has been investigated using both experimental and theoretical studies.

Organic Synthesis with α-Chloro Sulphides. Preparation of Aromatic γ-Lactones from Phenols and α-Chloro Sulphide Carboxylates

Lewis acid-catalysed alkylation of para-substituted phenols using α-chloro sulphides as electrophiles yields sulphenylated γ-lactones which can be desulphurised with zinc in acetic acid or Raney nickel.This synthesis has been applied to p-cresol, 2-naphthol, and two phenolic dihydrocinnamates.Alkylation of 1,4-dimethoxybenzene yields homogentisic acid dimethyl ether after desulphurisation and hydrolysis.

ORGANIC SYNTHESIS WITH α-CHLOROSULPHIDES. CONVERSION OF PHENOLS INTO γ-LACTONES USING METHYL-2-CHLORO-2-(ALKYL OR ARYLTHIO)CARBOXYLATES

Aromatic γ-lactones can be synthesised from 4-substitued phenols in a single step by zinc chloride-catalysed alkylation with methyl-2-chloro-2-(butylthio or phenylthio)propionate or acetate.

Thermal Rearrangement of 2-Methyl-2-(2'-acetoxy-5'-methylphenyl)oxirane

Thermal rearrangement of 2-methyl-(2'-acetoxy-5'-methylphenyl)oxirane (2) at 160 deg C for 1 hr furnishes a mixture of 2-(2'-hydroxy-5'-methylphenyl)propenyl acetate (4), 3,5-dimethylbenzofuran (11), 2-(2'-acetoxy-5'-methylphenyl)-propenyl acetate (5), 2-hydroxy-5-methylacetophenone (13), (+/-)-2,3-dihydro-3α,5-dimethylbenzofuran-2β-ol (14) and (+/-)-2,3-dihydro-3β,5-dimethylbenzofuran-2β-ol (15).Evidences in support of E-geometry at the ethylenic linkage of enolester (4) are presented.Treatment of 4 with alkali in the presence of air furnishes 13.Oxidation of a mixture of 14 and 15 gives 2,3-dihydro-3,5-dimethylbenzofuran-2-one (19). 3,5-Dimethylbenzofuran (11) has been prepared from 4.Thermal rearrangement of 2-methyl-(2'-acetoxy-5'-bromophenyl)oxirane (27) furnishes 5-bromo-3-methylbenzofuran (12) in good yield.