Question

Methylenedioxybenzene was subjected to Reaction 1, worked-up, then Reaction 2, worked up, and then Reaction 3. Following the work-up, the following NMR data was obtained. The molecular weight had increased by 100. Propose reagents for Reaction 1, Reaction 2, and then Reaction 3. 2 ? -3- -2-1 - 7 -2- 6 -1--1- 5 8 3 2 0 4 PPM AICI: CH3 CI A. E. AICI: B. NaBH4, ETOH, 25 °C F. EtOH, K2CO3, Reflux C. N2H4, KOH, EtOH, Reflux G. H2, Pd/C, EtOH, Reflux D. EtBr, HCI, Reflux TTT Arial 3 (12PTE. H. EtBr, K2CO3, Reflux

Answer 1

The final product is 1-(benzo[d][1,3]dioxol-4-yl)ethanol. This product is predicted based on the NMR given. According to the Scheme given inside the NMR there are only two steps but in the description it is mentioned as three steps. I analysed the problem based on the NMR (as final product). It required only two steps. Initially acetyl chloride addition (A) and then in second step reduction of the carbonyl to the hydroxy group (B). For the NMR analysis and structure of the final product and intermediates see the attachment.

Ho y ce NaBHAI EtoH Alda A HO + CH3 D H A: CH3,3H, doublet, 15 ppm B: C-H,1H, quantet, 4.9 ppm C: 0-H,1H, broad Singlet, 5'2 ppm D: CH2, 2H, Singlet, 60ppm e: Osomatic e-H, doublet, 14.618 ppm aromatic C-H, doublet, 2H, 6.9 PPM H #