Water → HCID 178442570, compound

HRID 980780Notes

Reaction equation

HRID 980780 reaction equation
[CH2:1]([C:9]1[S:13][C:12]2[S:14][C:15]([CH:17]=[O:18])=[CH:16][C:11]=2[CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:19]([CH:24]([CH2:27]O)[CH2:25][OH:26])[CH2:20][CH2:21][CH2:22][CH3:23].C1(C)C(S(O)(=O)=O)=CC=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([C:9]1[S:13][C:12]2[S:14][C:15]([C@H:17]3[O:26][CH2:25][C@H:24]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:27][O:18]3)=[CH:16][C:11]=2[CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 69252-Methylbenzenesulfonic acidHCID 1175092-Pentyl-1,3-propanediolHCID 202204675-n-Octylthieno[2,3-b]thiophene-2-carbaldehyde

Product 1

HCID 178442570HCID 178442570, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.4 g of 5-n-octylthieno[2,3-b]thiophene-2-carbaldehyde (obtainable from 2-n-octylthieno[2,3-b]thiophene by Vilsmeyer formylation with phosphorus oxychloride/dimethylformamide) and 9.5 g of 2-n-pentylpropane-1,3-diol are dissolved in 150 ml of toluene, a pinch of toluenesulfonic acid is added, and the mixture is heated under a water separator until water is no longer separated off. The acid is washed out with sodium bicarbonate solution, the organic phase is dried over sodium sulfate, and the toluene is distilled off. The pure trans-2-(5-n-octylthieno[2,3-b]thien-2-yl)-5-n-pentyl-1,3-dioxane is obtained by repeated recrystallization from ethanol (17.5 g).

Workup

  1. temperaturethe mixture is heated under a water
  2. customis no longer separated off
  3. washThe acid is washed out with sodium bicarbonate solution
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. distillationthe toluene is distilled off

Sources & evidence

ORD record
ord-c0e5f1949c2648158bb7199aad31aae6
Source dataset
uspto-grants-1987_01
Patent number
US04639328

Reaction notes

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