Methanol → HCID 69217978, compound

HRID 1471206Notes

Reaction equation

HRID 1471206 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:15]([O:17][CH3:18])=[O:16].C(O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].CO>C(O)(C)C>[CH:6]1[C:5]2[C:10](=[CH:1][C:2]([C:15]([O:17][CH2:18][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])=[O:16])=[CH:3][CH:4]=2)[CH:9]=[CH:8][C:7]=1[C:11]([O:13][CH2:14][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 8221Stearyl AlcoholHCID 61225Dimethyl-2,6-naphthalenedicarboxylate

Product 1

HCID 69217978HCID 69217978, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
160 °C

Procedure

To a 3 neck 100 mL round bottomed flask equipped with a Dean Stark trap and condenser, thermocouple and argon inlet was added dimethyl naphthalene-2,6-dicarboxylate (10 grams, 40.94 mmoles, available from Sigma Aldrich),stearyl alcohol (22.15 grams, 81.89 mmoles, available from Spectrum Chemical), Fascat 4100 (0.03 grams, 0.1 wt %, available from Arkema Inc) and Xylenes (50 ml, available from Sigma Aldrich). The mixture was slowly heated under argon to 160° C. during which reagents melted/dissolved. The temperature was raised to 180° C. The reaction mixture was stirred at 180° C. overnight (˜20 hours) during which 46 mL of a mixture of xylenes and methanol was collected. Vacuum was applied (1-2 mm-Hg) for about 10 minutes during which an additional 5 mL of a mixture of Xylenes and methanol was collected. The solution was cooled under argon to about 140° C. and discharged in an aluminum tray where it was allowed to cool to room temperature to give product as an off-white solid. The product was transferred to a 1 L Erlenmeyer flask, about 100 mL of isopropyl alcohol was added, heated to about 100° C. during which product dissolved. The solution was cooled to room temperature during which product crystallized out, filtered and dried on a vacuum pump overnight to give 25.33 grams product as an off-white solid (86% yield). The product was shown to be pure by 1H NMR with trace amounts of the mono-ester. Physical properties of this compound are shown in Table 2 above. The FIGURE shows the rheological profile.

Workup

  1. customTo a 3 neck 100 mL round bottomed flask equipped with a Dean Stark trap and condenser, thermocouple and argon inlet
  2. dissolutionmelted/dissolved
  3. temperatureThe temperature was raised to 180° C
  4. customwas collected
  5. customfor about 10 minutes
  6. customwas collected
  7. temperatureThe solution was cooled under argon to about 140° C.
  8. temperatureto cool to room temperature
  9. customto give product as an off-white solid
  10. additionwas added
  11. temperatureheated to about 100° C. during which product
  12. dissolutiondissolved
  13. temperatureThe solution was cooled to room temperature during which product
  14. customcrystallized out
  15. filtrationfiltered
  16. customdried on a vacuum pump overnight

Sources & evidence

ORD record
ord-1837350b0ba74b948f0f119a451e4d77
Source dataset
uspto-grants-2015_04
Patent number
US09011587B1

Reaction notes

Loading…