Triethylamine → HCID 14986286, compound

HRID 1613039Notes

Reaction equation

HRID 1613039 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:9]=1[OH:15].C(N([CH2:21][CH3:22])CC)C.[CH3:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:28](=[O:29])[C:27]2[CH:31]=[CH:32][C:24]([CH3:23])=[CH:25][CH:26]=2)[C:9]=1[O:15][C:9](=[O:15])[C:8]1[CH:13]=[CH:12][C:21]([CH3:22])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 149862841-(6-Bromohexyl)-2,3-dihydroxybenzene

Product 1

HCID 14986286HCID 14986286, compoundYield 180.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 9.0 g (0.033 mol) of 1-(6-bromohexyl)-2,3-dihydroxybenzene in 200 mL of anhydrous tetrahydrofuran and 13.7 mL (0.099 mol) of triethylamine stirred in an ice bath was added 10.9 mL (0.082 mol) of 4-methylbenzoyl chloride dropwise over 30 minutes. After 30 minutes, the bath was removed and stirring was continued at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure, the residue was treated with sodium bicarbonate and the product was extracted with ether. The dried extract was concentrated to an oil which was purified by HPLC using 10% ethyl acetate-hexane to give 15.2 g (90% yield) of 1-(6-bromohexyl)-2,3-bis[(4-methylbenzoyl)oxy]benzene as an oil.

Workup

  1. customthe bath was removed
  2. waitwas continued at room temperature for 2.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was treated with sodium bicarbonate
  5. extractionthe product was extracted with ether
  6. extractionThe dried extract
  7. concentrationwas concentrated to an oil which
  8. customwas purified by HPLC

Sources & evidence

ORD record
ord-d367db37da354901995b425fc821120a
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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