1-Bromodecane → HCID 86638314, compound

HRID 882554Notes

Reaction equation

HRID 882554 reaction equation
O[C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:23]([O-:26])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:13]([O:11][C:6]1[CH:7]=[C:8]([O:10][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:9]=[C:2]([O:26][CH2:23][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:3]=1[CH:4]=[O:5])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 81731-Bromodecane2×HCID 11430Potassium CarbonateHCID 68099Benzaldehyde, 2,4,6-trihydroxy-

Product 1

HCID 86638314HCID 86638314, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2,4,6-trihydroxybenzaldehyde (3.00 g, 19.5 mmol), 1-bromodecane (25.87 g, 117.0 mmol), K2CO3 (8.07 g, 58.4 mmol), and KI (549 mg, 3.3 mmol) in DMF (150 mL) was stirred for 24 h at 110° C. and then one more portion of 1-bromodecane (5.0 g, 22.6 mmol) was added and continued stirring for another 24 h. The reaction mixture was cooled to 20° C. and extracted with CH2Cl2. The organic phase was washed with brine, dried (Na2SO4), and evaporated. Column chromatography (silica gel, hexane/CH2Cl2, 1:1, v/v) afforded the product (9.86 g, 88%) as yellow oil.

Workup

  1. stirringcontinued stirring for another 24 h
  2. temperatureThe reaction mixture was cooled to 20° C.
  3. extractionextracted with CH2Cl2
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-273fe3a21b334767b1ecf4ebbeb6d73d
Source dataset
uspto-grants-2015_03
Patent number
US08993804B2

Reaction notes

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