Water → HCID 18987360, compound

HRID 2380345Notes

Reaction equation

HRID 2380345 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:10]=[C:11]([OH:21])[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].O>CN(C)C=O>[C:3]1([C:9]2[CH:10]=[C:11]([CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[O:21][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 35546253,5-diphenylphenol

Product 1

HCID 18987360HCID 18987360, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.78 g of sodium hydride (55% w/w dispersion in mineral oil) in 300 cc of dimethylformamide was added a solution of 2 g of 3,5-diphenyl-phenol in 10 cc of dimethylformamide. The mixture was stirred for 5 hours at room temperature until effervescence had stopped. 2.2 g of ethyl 6-bromohexanoate was then added and the resultant mixture stirred at room temperature overnight. The mixture was then heated for 20 hours to 40° C. After cooling, the resultant mixture was poured into 100 cc of cold water and extracted with ethyl acetate (3#100 cc). The combined extracts were washed with water, dried (Na2SO4) and concentrated in vacuo. The resultant residue was flash chromatographed on silica gel (30-60 mm; eluent: 92:8 n-hexane/ethyl acetate) to give 1 g of ethyl 6-(3,5-diphenyl-phenoxy)hexanoate as a oil, used without further purification in the next step.

Workup

  1. temperatureThe mixture was then heated for 20 hours to 40° C
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (3#100 cc)
  4. washThe combined extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customchromatographed on silica gel (30-60 mm; eluent: 92:8 n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bb0e69a9ef9445a4a8860ce1b8a95816
Source dataset
uspto-grants-1994_11
Patent number
US05366982

Reaction notes

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