Potassium Hydroxide → HCID 19808864, compound

HRID 373985Notes

Reaction equation

HRID 373985 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:18]3[C:13](=[C:14]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:15]=[CH:16][C:17]=3[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:11]([C:43](OC)=[O:44])[C:10]=2[C:47]([O:49]C)=[O:48])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>O.CO.C1COCC1>[C:1]1([CH2:7][O:8][C:9]2[C:10]3[C:47](=[O:48])[O:49][C:43](=[O:44])[C:11]=3[C:12]([O:35][CH2:36][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[C:13]3[C:18]=2[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:16][CH:15]=[C:14]3[O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 438021Dimethyl 1,4,5,8-tetrakis(phenylmethoxy)-2,3-naphthalene dicarboxylate

Product 1

HCID 19808864HCID 19808864, compoundYield 76.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

12.50 g of dimethyl 1,4,5,8-tetrakis(phenylmethoxy)-2,3-napthalene dicarboxylate prepared in Step 2A-c above was refluxed with 12.0 g of KOH in 24 mL of water, 300 mL of methanol and 100 mL of THF for 1 hour. The solvent was removed, and the residue acidified with 1N HCl. The solid was then collected by filtration and was refluxed in 55 mL of acetic anhydride for 30 minutes. After cooling to room temperature, a mixed solvent of 1:1 v/v diethyl ether and petroleum ether was added. The yellow crystalline solid was collected by filtration to yield 8.94 g of the title compound.

Workup

  1. customThe solvent was removed
  2. filtrationThe solid was then collected by filtration
  3. temperaturewas refluxed in 55 mL of acetic anhydride for 30 minutes
  4. additiona mixed solvent of 1:1 v/v diethyl ether and petroleum ether was added
  5. filtrationThe yellow crystalline solid was collected by filtration

Sources & evidence

ORD record
ord-ae85f5071afc446db3a6c32c5aca526b
Source dataset
uspto-grants-1992_11
Patent number
US05166208

Reaction notes

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