Vanillic Acid → HCID 67234166, compound

HRID 1895892Notes

Reaction equation

HRID 1895892 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28]>CN(C)C=O>[OH:8][C:7]1[CH:9]=[CH:10][C:2]([C:1]([O:12][CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=[CH2:23])=[O:11])=[CH:3][C:4]=1[O:5][CH3:6]

Participants

5

Reactant 3

HCID 8468Vanillic AcidHCID 759066-Bromo-1-hexeneHCID 81531Diisopropylethylamine

Product 1

HCID 67234166HCID 67234166, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of vanillic acid (0.6 g, 3.56 mmol) in N,N-dimethylformamide (7 ml), diisopropylethylamine (0.93 ml, 5.35 mmol) and 6-bromohex-1-ene (0.71 ml, 5.35 mmol) were added. The reaction was stirred at 50° for 8 hours. The solvent was evaporated under vacuum. The residue was purified by flash chromatography (Biotage System, column FLASH 40+M™ KP-Sil, eluent: gradient n-hexane/ethyl acetate 95/5 (200 ml), to n-hexane/ethyl acetate 7/3 during 2000 ml, n-hexane/ethyl acetate 3/7 (400 ml)). The product (0.59 g) was obtained.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customThe residue was purified by flash chromatography (Biotage System, column FLASH 40+M™ KP-Sil, eluent: gradient n-hexane/ethyl acetate 95/5 (200 ml), to n-hexane/ethyl acetate 7/3 during 2000 ml, n-hexane/ethyl acetate 3/7 (400 ml))

Sources & evidence

ORD record
ord-4805a9d57dcf430f87af06891da6f4f7
Source dataset
uspto-grants-2013_08
Patent number
US08518920B2

Reaction notes

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