2-Bromo-2'-acetonaphthone → 4-Hydroxy-undecanoic acid-2-naphthalen-2-yl-2-oxo-ethyl ester

HRID 1384414Notes

Reaction equation

HRID 1384414 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[Na+].[OH:16][CH:17]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:18][CH2:19][C:20]([O-:22])=[O:21]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.CCOCC>[CH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:5]=1[C:3](=[O:4])[CH2:2][O:22][C:20](=[O:21])[CH2:19][CH2:18][CH:17]([OH:16])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 2

HCID 691792-Bromo-2'-acetonaphthoneHCID 23710311Sodium 4-hydroxyundecanoate

Product 1

HCID 211868244-Hydroxy-undecanoic acid-2-naphthalen-2-yl-2-oxo-ethyl esterYield 26.6%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 20.00 g of 2-bromo-2′-acetonaphtone, 18.01 g of 4-hydroxy-undecanoic acid sodium salt, and 0.5 g of tetrabutylammonium bromide in 180 ml of dimethylformamide was stirred for 6 hours at 50° C. Then, the reaction mixture was diluted with ether and washed with water, 2N HCl, saturated sodium bicarbonate, and brine. Then, the mixture was dried, filtered, and evaporated to dryness. The resulting solid was purified by recrystallization to yield 7.92 g of colorless crystals.

Workup

  1. washwashed with water, 2N HCl, saturated sodium bicarbonate, and brine
  2. customThen, the mixture was dried
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting solid was purified by recrystallization

Sources & evidence

ORD record
ord-5d944f93216e431c903ea25801bde7b8
Source dataset
uspto-grants-2001_07
Patent number
US06258854B1

Reaction notes

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