KBS14-9 - Methyl esterification of ferrocenecarboxylic acid about usyd_phd_eln

[KlementineJBS]

16.06.22

1. Cooled methanol (9 mL) over ice
2. Added acetyl chloride (0.35 mL, 4.91 mmol, 1.2 equiv.) and stirred 15 minutes
3. Added ferrocenecarboxylic acid (926 mg, 4.03 mmol)
4. Heated to reflux from 11.50 am
5. TLC'd at 1.30 and 4.30 pm
6. Left overnight

[KlementineJBS]

17.06.22

7. TLC'd at 10 am
8. Quenched with NaHCO3 (40 mL) and NaOH (10 mL) until pH ~12
9. Rotovapped down using toluene (3 x 40 mL) to azeotrope off methanol

NOTE: could try rotovapping prior to quenching, but must use toxics cupboard (due to HCl gas production)

Vial (empty) = 15.5735
Vial (product) = 15.9069
Mass = 333.4 mg

[KlementineJBS]

20.06.22

H NMR

KBS14-9 cr_1.zip

KBS14-9 cr processed.pdf

1H NMR (300 MHz, Chloroform-d) δ 4.81 (t, 2H), 4.40 (t, 2H), 4.21 (s, 5H), 3.81 (s, 3H).

Contains mostly product but with considerable junk - will need columning.

Column

F1-4

Vial (empty) = 15.6733
Vial (full) = 15.8394
Mass = 166.1 mg

KBS14-9 F1-4_1.zip

KBS14-9 F1-4 processed.pdf

F5-7

Vial (empty) = 15.7287
Vial (full) = 15.7568
Mass = 28.1 mg

KBS14-9 F5-7_1.zip

KBS14-9 F5-7 processed.pdf