52213-49-7

Upstream product

• 2746-25-0 p-Methoxybenzyl bromide 
• 7291-34-1 2-methoxy-N,N-dimethylbenzamide 
• 123-11-5 4-methoxy-benzaldehyde 
• 82780-49-2 2-[2-Hydroxy-2-(4-methoxy-phenyl)-ethyl]-6-methoxy-N,N-dimethyl-benzamide 
• 82780-48-1 N,N-Dimethyl-2-methoxy-6-methylbenzamide 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 53015-08-0 2-formyl-6-methoxy-benzoic acid 
• 28281-58-5 7-methoxyisobenzofuran-1(3H)-one 
• 71885-44-4 4,5-dihydro-4,4-dimethyl-2-(2-methylphenyl)-2-oxazoline 
• 400781-21-7 (+/-)-3-(4-methoxybenzyl)-7-methoxyphthalide 
• 82780-51-6 (+/-)-3-(4-methoxyphenyl)-8-methoxy-3,4-dihydroisocoumarin 
• 113345-85-0 3,4'-dimethylstilbene-2-carboxylic acid 

Relevant academic research and scientific papers

Synthesis of 3-substituted 8-hydroxy-3,4-dihydroisocoumarins via successive lateral and ortho-lithiations of 4,4-dimethyl-2-(o-tolyl)oxazoline

Sequential treatment of 4,4-dimethyl-2-(o-tolyl)oxazoline in THF with sec-BuLi, aromatic or aliphatic aldehydes, sec-BuLi, B(OMe)3, and H2O2 produced the laterally alkylated and ortho-hydroxylated oxazolines in one-pot. Treatment of these products with TFA in aqueous THF provided 3-substituted 8-hydroxy-3,4-dihydroisocoumarins in 44-75% overall yields. This procedure allowed the short synthesis of (±)-hydrangenol and (±)-phyllodulcin, naturally occurring 3,4-dihydroisocoumarins of pharmacological interest. A more economical synthesis of (±)-phyllodulcin via the trianion intermediate is also described.

Expedient syntheses of naturally occurring ±-3-benzylphthalides and ±-3-aryl-8-hydroxy-3,4-dihydroisocoumarins: Structure revision of the ±-3-benzylphthalide isolated from Frullania falciloba

A simple synthesis of ±-3-benzyl-7-methoxyphthalides (1b,1d and 4a-c) from 7-methoxyphthalides (3a-c) and a novel AlCl3-catalysed conversion of ±-3-benzyl-7-methoxyphthalides (1d,4a-c) to 4′-O-methylhydrangenol 5a, 4′,6-O,O-dimethylthunberginol

Convenient syntheses of 3-aryl-3,4-dihydroisocoumarins and lunularic acid derivatives

A convenient two-step approach for the syntheses of 3-aryl-3,4-dihydroisocoumarins (13-17) including some naturally occurring 3-aryl-8-hydroxy-3,4-dihydroisocoumarins (1,2) and lunularic acid derivatives (18-21) is described from 2-formylbenzoic acids (4,

Ortho-Lithiated Tertiary Benzamides. Chain Extension via o-Toluamide Anion and General Synthesis of Isocoumarins Including Hydrangenol and Phyllodulcin

Lithiation of N,N-diethyl-2-methylbenzamide (2a) followed by condensation with aromatic aldehydes and basic hydrolysis leads to 3-aryl-3,4-dihydroisocoumarins 4 in modest overall yields.Adoption of this methodology to N,N-dimethyl-2-methyl-6-methoxybenzamide (7b) provides isocoumarins 9a and 9b which by selective demethylation procedures yields hydrangenol (10a) and phyllodulcin (10c), naturally occurring isocoumarins of pharmacological interest.A one-pot, abbreviated procedure for the preparation of both 9a and 9b starting with N,N-Dimethyl-2-methoxybenzamide (6c) is also described.