تفاعل #705261

معادلة التفاعل

3,4-dihydro-4,4-dimethyl-6-acetyl-1(2H)-naphthalenone

ethylene glycol

p-toluenesulfonic acid monohydrate

3,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone

Compound 100C

3,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone

Compound 100D

3,4-dihydro-4,4-dimethyl-6-acetyl-1(2H)-naphthalenone

→

title compound

4-[(5,6-dihydro-5,5-dimethyl-8-(2-furyl)-2-naphthalenyl)ethynyl]benzoic acid

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe resulting solution was heated
2. 2
   درجة الحرارةto reflux for 18 hours
3. 3
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

A solution of 1.80 g (8.34 mmol) of a 1:5 mixture of 3,4-dihydro-4,4-dimethyl-7-acetyl-1(2H)-naphthalenone (Compound 100C); and 3,4-dihydro-4,4-dimethyl-6-acetyl-1(2H)-naphthalenone (Compound 100D) in 50 ml benzene was combined with 517.7 mg (8.34 mmol) of ethylene glycol and 20.0 mg (0.11 mmol) of p-toluenesulfonic acid monohydrate. The resulting solution was heated to reflux for 18 hours, cooled to room temperature, and concentrated under reduced pressure. The title compound was isolated by column chromatography (10% EtOAc-hexanes) as a colorless oil. 1H NMR (CDCl3): δ 8.01 (1H, d, J=8.2 Hz), 7.51 (1H, s), 7.43 (1H, dd, J=1.7, 6.4 Hz), 4.07 (2H, m), 3.79 (2H, m), 2.74 (2H, t, J=6.5 Hz), 2.04 (2H, t, J=7.1 Hz), 1.67 (3H, s), 1.46 (6H, s).

المصدر