Hydrochloric Acid → HCID 69956801, compound

HRID 2186510Notes

Reaction equation

HRID 2186510 reaction equation
[S:1]1[C:5]2[C:6]3[CH:11]=[CH:10][S:9][C:7]=3[S:8][C:4]=2[CH:3]=[CH:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[C:16](Cl)(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].Cl>ClCCl>[C:16]([C:2]1[S:1][C:5]2[C:6]3[CH:11]=[CH:10][S:9][C:7]=3[S:8][C:4]=2[CH:3]=1)(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8124Octanoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 13708387HCID 13708387, compound

Product 1

HCID 69956801HCID 69956801, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Dithienothiophene 2 (R1=R2=R3=R4=H) (765 mg, 3.90 mmol) was dissolved in dry dichloromethane (35 cm3) and the solution was ice-cooled before AlCl3 (790 mg, 5.92 mmol) was added in one portion yielding a dark mixture. A solution of octanoyl chloride (1.00 g, 6.02 mmol) in dichloromethane (20 cm3) was added dropwise over a 20 minute period and the mixture was then allowed to stand at room temperature For a further thirty minutes. It was hen added to ice and the mixture was acidified with dilute hydrochloric acid (100 cm3). Additional dichloromethane (100 cm3) was added and the layers separated. The organic layer was washed with water, dried over MgSO4 and concentrated. Column Chromatography (hexane—30% dichloromethane/hexane) afforded 790 mg (63%) of the title compound. An analytical sample may be prepared by recrystallisation from a mixture of dichloromethane and methanol. Rf 0.31 (1:1 dichloromethane/hexane); m.p. 130-131° C.; 1H (250 MHz, CDCl1) δ0.89 (3H, t, J6.5, CH2CH3); 1.25 (8H, br s, CH2CH2CH2); 1.78 (2H, m, CH2CH2CO); 2.93 (2H, t, J7.5, CH2CO); 7.32 (1H, d, J5.0, Dt-H); 7.52 (1H, d, J5.0, Dt-H); 7.91 (1H, s, Dt-H); 13C (100 MHz, CDCl3) δ14.1; 22.6; 25.0; 29.1; 29.3; 30.9; 31.7; 39.0; 120.9; 125.5; 129.0; 141.4; 144.4; 144.9; 193.7; v (cm−1, KBr) 600, 702, 1191, 1364, 1466, 1493, 1644 (C=O), 2925; Calc. for C16H18S3O C: 59.6; H: 5.6; Found: C: 59.2; H: 5.6.

Workup

  1. additionwas added in one portion
  2. customyielding a dark mixture
  3. waitto stand at room temperature For a further thirty minutes
  4. additionadded to ice
  5. customthe layers separated
  6. washThe organic layer was washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-33380e8b34344fb383957fd3adb34462
Source dataset
uspto-grants-2002_06
Patent number
US06403809B1

Reaction notes

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