Benzene → HCID 15003162, compound

HRID 2291877Notes

Reaction equation

HRID 2291877 reaction equation
[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18](S(O)(=O)=O)=[CH:17][CH:16]=1.[CH:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH:1]([O:9][CH2:10][CH3:11])[C:2]#[C:26][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:15][CH3:25])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 9834203HCID 9834203, compound

Product 1

HCID 15003162HCID 15003162, compound

Procedure

32 g of ethane-2,2'-[2-pentadecyn-1-ylidene bis(oxy)]bis, 25 g of 4-benzoyloxy-1-butanol, and 100 mg of p-toluene sulfonic acid were refluxed in a dry apparatus in 300 ml of benzene using a Dean-Stark trap. After evaporating 75 ml of solvent, the solution was cooled to room temperature diluted with CHCl3, washed with saturated aqueous NaHCO3, then with water and dried over Na2SO4. The resulting oil (13 g) after evaporation of the solvent was purified by column chromatography (SiO2) (CHCl3). The partially purified compound was rechromatographed (SiO2) (50% Hexanes/CHCl3). Yield: 1.5 g.

Workup

  1. customAfter evaporating 75 ml of solvent
  2. additiondiluted with CHCl3
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialwith water and dried over Na2SO4
  5. customThe resulting oil (13 g) after evaporation of the solvent
  6. customwas purified by column chromatography (SiO2) (CHCl3)
  7. customThe partially purified compound was rechromatographed (SiO2) (50% Hexanes/CHCl3)

Sources & evidence

ORD record
ord-c28a66ec6fc645519cf8d34f4469fb9c
Source dataset
uspto-grants-1989_01
Patent number
US04798842

Reaction notes

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