Resorcinol → HCID 13796229, compound

HRID 1885887Notes

Reaction equation

HRID 1885887 reaction equation
[H-].[Na+].[C:3]1([CH:10]=[CH:9][CH:8]=[C:6]([OH:7])[CH:5]=1)[OH:4].[I-].[Na+].[CH2:13](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C)C=O.O1CCCC1>[CH2:28]([O:4][C:3]1[CH:5]=[C:6]([OH:7])[CH:8]=[CH:9][CH:10]=1)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

Participants

7

Reactant 4

HCID 5054ResorcinolHCID 5238Sodium IodideHCID 82131-BromohexadecaneHCID 24758Sodium hydride

Product 1

HCID 13796229HCID 13796229, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 29.6 g of sodium hydride in 215 ml of N,N-dimethylformamide was added dropwise over 1.5 hours a solution of 54.33 g of resorcinol in 145 ml of N,N-dimethylformamide and 72 ml of tetrahydrofuran. The resulting mixture was cooled to 0° C. and 7.4 g of sodium iodide added followed by the dropwise addition of 155.0 g of hexadecylbromide over 1 hour. The bath was removed and the mixture stirred at ambient temperature for 17 hours. The mixture was diluted with 500 ml of iced dilute hydrochloric acid, extracted with ether and filtered. The ether layer was dried over magnesium sulfate and evaporated to an oil which was purified by chromatography on silica gel using ethyl acetate-hexanes giving 37.2 g of the desired compound as a white solid, m.p. 58°-59° C.

Workup

  1. customThe bath was removed
  2. additionThe mixture was diluted with 500 ml of iced dilute hydrochloric acid
  3. extractionextracted with ether
  4. filtrationfiltered
  5. dry with materialThe ether layer was dried over magnesium sulfate
  6. customevaporated to an oil which
  7. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-02ef8987739e4b19b7c720eee9177ec4
Source dataset
uspto-grants-1992_09
Patent number
US05147864

Reaction notes

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