Toluene → HCID 20798726, compound

HRID 1071885Notes

Reaction equation

HRID 1071885 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1O.[C:13]1(=[O:19])[O:18][C:16](=[O:17])C=C1.ClC1C=CC=CC=1Cl.C1(C)C=CC=CC=1.[C:35](OCC)(=[O:37])[CH3:36]>>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[CH:8]3[CH2:36][C:35](=[O:37])[CH:5]([CH:6]4[C:16](=[O:17])[O:18][C:13](=[O:19])[CH:7]43)[C:4]=2[CH:3]=1

Participants

6

Reactant 5

HCID 1140TolueneHCID 72391,2-DichlorobenzeneHCID 7923Maleic AnhydrideHCID 8857Ethyl Acetate2×HCID 113181,2-Dihydroxynaphthalene

Product 1

HCID 20798726HCID 20798726, compoundYield 16%

Conditions

Temperature
90 °C

Procedure

A solution of dihydroxynaphthalene (500 g, 3.125 mol) and maleic anhydride (765 g, 7.815 mol, 2.5 eq) in 1 L 1:1 1,2-dichlorobenzene:toluene were heated at 110° C. for 3 days. The reaction mixture was then cooled to 90° C., 1.5 L ethyl acetate added, and then further cooled to room temperature overnight. The mixture was then cooled over ice after another 0.5 L ethyl acetate was added and left stirring for 2 hours. The resultant solid was isolated by filtration, washed with 2×200 mL cold ethyl acetate and dried in oven at 40° C. to provide 130 g of the anhydride as a beige solid (16% yield). 1H NMR (acetone-d6) 7.33 (d, J=8.2 Hz, 1H), 6.97 (d, J=2.3 Hz, 1H), 6.85 (dd, J=8.1, 2.4 Hz, 4.05 (d, J=3.9 Hz, 1H), 3.98 (dd, J=6.0, 2.9 Hz, 1H), 3.88 (dd, J=10.2, 3.9 Hz, 1H), 3.70 (dd, J=10.2, 2.7 Hz, 1H), 2.39 (br s, 2H). HRMS for MH+259.0600 (theoretical 259.0606).

Workup

  1. temperaturefurther cooled to room temperature overnight
  2. additionwas added
  3. waitleft
  4. customThe resultant solid was isolated by filtration
  5. washwashed with 2×200 mL cold ethyl acetate
  6. customdried in oven at 40° C.

Sources & evidence

ORD record
ord-088fd2728bd4455ab6e771a405d4c4e9
Source dataset
uspto-grants-2005_06
Patent number
US06906046B2

Reaction notes

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