Benzyl Bromide → Dimethyl 1,4,5,8-tetrakis(phenylmethoxy)-2,3-naphthalene dicarboxylate

HRID 373984Notes

Reaction equation

HRID 373984 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:8]=[CH:9][C:10]=2[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]([OH:28])=[C:4]([C:29]([O:31][CH3:32])=[O:30])[C:3]=1[C:33]([O:35][CH3:36])=[O:34].C(=O)([O-])[O-].[K+].[K+].[CH2:43](Br)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CN(C)C=O.CC(C)=O>[C:44]1([CH2:43][O:28][C:5]2[C:6]3[C:11](=[C:10]([O:12][CH2:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:9]=[CH:8][C:7]=3[O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:2]([O:1][CH2:33][C:3]3[CH:4]=[CH:5][CH:6]=[CH:11][CH:2]=3)=[C:3]([C:33]([O:35][CH3:36])=[O:34])[C:4]=2[C:29]([O:31][CH3:32])=[O:30])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19808875HCID 19808875, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.00 g of dimethyl 1,4-dihydroxy-5,8-bis(phenylmethoxyl)-2,3-naphthalene dicarboxylate prepared in Step 2A-b above, 12.00 g of potassium carbonate and 8.0 mL of benzyl bromide in 100 mL of dimethyl formamide and 200 mL of acetone was stirred at room temperature for 2 days. The reaction was filtered. The filtrate was then concentrated and the solid was washed with mixed solvent of ethyl acetate and petroleum ether to give 12.50 g of the title compound as a yellow solid.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationThe filtrate was then concentrated
  3. washthe solid was washed with mixed solvent of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-089ca9c6fbb94e4b9196868f68276079
Source dataset
uspto-grants-1992_11
Patent number
US05166208

Reaction notes

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