Resorcinol → HCID 19375818, compound

HRID 2211369Notes

Reaction equation

HRID 2211369 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].Br[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[OH:2][C:1]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[O:5][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 3

HCID 5054ResorcinolHCID 11430Potassium CarbonateHCID 79557Methyl 5-bromovalerate

Product 1

HCID 19375818HCID 19375818, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 11 g of resorcinol, 8.8 g of methyl 5-bromopentanoate, and 13.8 g of potassium carbonate in 150 mL of dimethylformamide was heated in an oil bath at 90° C. for 24 hours. The mixture was cooled, diluted with water, and extracted with ethyl acetate. The organic phase was washed with water, washed with saturated sodium chloride, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl ether providing the title intermediate in 34% yield, NMR.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with hexane/ethyl ether providing the title intermediate in 34% yield, NMR

Sources & evidence

ORD record
ord-80d2064ddebb4ab0a86ebe68391dd989
Source dataset
uspto-grants-1995_10
Patent number
US05462954

Reaction notes

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