Veratrole → HCID 14986288, compound

HRID 2108254Notes

Reaction equation

HRID 2108254 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:9][CH3:10])[CH:5]=1)=[O:18]

Participants

5

Reactant 4

HCID 7043VeratroleHCID 9845Trifluoroacetic anhydrideHCID 202106-Bromohexanoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 14986288HCID 14986288, compoundYield 65.1%

Procedure

A mixture of 1.0 mL (7.8 mmol) of 1,2-dimethoxybenzene and 2.0 g (10 mmol) of 6-bromohexanoic acid was warmed briefly until homogeneous and stirred while 1.7 mL (11.7 mmol) of trifluoroacetic anhydride was added. The reaction mixture was stirred at room temperature for 17 hours and then was poured into sodium bicarbonate solution. The product was extracted with ethyl acetate and the dried extract was concentrated to an oil which was purified by chromatography on 150 g of silica gel. Elution with 25% ethyl acetate-hexane gave 1.6 g (65% yield) of 1-(6-bromo-1-oxohexyl)-3,4-dimethoxybenzene. The nmr spectrum was consistent with the structure.

Workup

  1. temperaturewas warmed briefly until homogeneous and
  2. additionwas added
  3. extractionThe product was extracted with ethyl acetate
  4. extractionthe dried extract
  5. concentrationwas concentrated to an oil which
  6. customwas purified by chromatography on 150 g of silica gel
  7. washElution with 25% ethyl acetate-hexane

Sources & evidence

ORD record
ord-137ed8b769574dfa8c25ec3a2085ab54
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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