Toluene → HCID 19062989, compound

HRID 482510Notes

Reaction equation

HRID 482510 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:25]#[C:26][C:27]4[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:37]1(C)C=CC=CC=1.[OH-].[Na+].S(OC)(OC)(=O)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]12([C:11]3[CH:12]=[C:13]([C:25]#[C:26][C:27]4[CH:28]=[CH:29][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:35][CH:36]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH3:37])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

7

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 19063054Methyl 4-[3-(1-adamantyl)-4-(6-hydroxyhexyloxy)phenylethynyl]benzoate

Product 1

HCID 19062989HCID 19062989, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

390 mg (0.8 mmol) of methyl 4-[3-(1-adamantyl)-4-(6-hydroxyhexyloxy)phenylethynyl]benzoate, 10 ml of toluene and 200 μl of a 50% sodium hydroxide solution were introduced into a round-bottomed flask. 20 mg (5.4 mmol) of tetrabutylammonium iodide and 100 μl (0.9 mmol) of dimethyl sulfate were added and stirring was carried out at room temperature for four hours. The reaction mixture was poured into water and extracted with ethyl acetate and the organic phase was separated by settling, dried over magnesium sulphate and evaporated.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase was separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-2c14412a6f864da8bd16effb984bce5a
Source dataset
uspto-grants-1998_08
Patent number
US05798354

Reaction notes

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