Benzyl Bromide → Diethyl 1,4-bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate

HRID 222422Notes

Reaction equation

HRID 222422 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([OH:20])=[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:2]1([CH2:1][O:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([O:20][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 431092,3-Diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate

Product 1

HCID 58012491Diethyl 1,4-bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylateYield 109.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzylbromide (2.95 ml, 24.7 mmol) was added to a stirred solution of diethyl 1,4-dihydroxy-2,3-naphthalenedicarboxylate (3 g, 9.87 mmol) and potassium carbonate (3.40 g, 24.7 mmol) in acetone (100 ml). The reaction mixture was refluxed for 18 hours under an atmosphere of argon. The resulting mixture was evaporated and the reaction mixture triturated with water. The resulting tan coloured solid was collected by filtration and washed with water then dried under vacuum to give the title compound (5.23 g, 10.8 mmol). LC/MS: Rt=4.13, [MH]+ 485.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours under an atmosphere of argon
  2. customThe resulting mixture was evaporated
  3. customthe reaction mixture triturated with water
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customthen dried under vacuum

Sources & evidence

ORD record
ord-eb2e70f17c5e40159395eb9eab2a6260
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

Loading…