Dimethylformamide → HCID 15086653, compound

HRID 2108269Notes

Reaction equation

HRID 2108269 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10](O)[CH:9]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+].CN(C)C=O>CC(C)=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]([O:27][CH2:24][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium Carbonate2×HCID 15086652HCID 15086652, compound

Product 1

HCID 15086653HCID 15086653, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8.3 g (0.030 mol) of 1-(6-bromohexyl)-3,4-dihydroxybenzene, 18 mL (0.15 mol) of benzyl bromide and 13 g (0.09 mol) of potassium carbonate in 160 mL of acetone-50 mL of dimethylformamide was stirred at reflux for 24 hours. Potassium carbonate (4 g) was added and stirring at reflux was continued for 48 hours. The reaction mixture was cooled, filtered and the filtrate was concentrated at reduced pressure to an oil. Purification by HPLC using 1% ethyl acetate-hexane gave 6.4 g (47% yield) of 1-(6-bromohexyl)-3,4-bis-(phenylmethoxy)benzene. The nmr spectrum was consistent with the structure and the low resolution mass spectrum showed the molecular ion at m/z 452 (C26H29BrO2).

Workup

  1. temperatureat reflux for 24 hours
  2. stirringstirring
  3. temperatureat reflux
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated at reduced pressure to an oil
  7. customPurification by HPLC

Sources & evidence

ORD record
ord-fa5327d266b841dfaa5d5d0228f8e518
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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