Acetyl chloride → 1-(4,4-Dimethylthiochroman-6-yl)ethanone

HRID 1762726Notes

Reaction equation

HRID 1762726 reaction equation
[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5][CH2:4][CH2:3]1.[C:13](Cl)(=[O:15])[CH3:14].[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[C:13]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[S:5][CH2:4][CH2:3][C:2]2([CH3:12])[CH3:1])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 110194304,4-Dimethylthiochroman

Product 1

HCID 117083551-(4,4-Dimethylthiochroman-6-yl)ethanoneYield 87.8%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

A solution of 10.0 g (0.056 mol) of 4,4-dimethylthiochroman and 4.4 g (0.056 mol) of acetyl chloride in 150 mL of CS2 was added dropwise over a 45-minutes period to a stirred CS2 suspension of AlCl3 (11.22 g, 0.084 mol) in a 500-mL, round-bottom flask equipped with a condenser and nitrogen inlet. The resulting yellowish-orange mixture was allowed to stir for 10 hours at room temperature; 80 mL of ice water was added and the two layers separated. The aqueous layer was extracted with ether (3×50 mL); the ether layers were combined and dried (Na2SO4, 6 h). After evaporation, the resulting light yellow oil was vacuum distilled to give 10.83 grams (87.6%) of 6-acetyl-4,4-dimethylthiochroman as a yellowish viscous oil: bp 168°-173° C./1.0 mm; IR (neat) 1680 cm-1 ; 1H NMR (DCCl3 δ1.31 [s, 6 H, (CH)3)2 C], 1.89 [m, 2 H, ArSCH2CH2 ], 2.52 [s, 3 H, CH3C=O]3.01 [m, 2 H, ArSCH2CH2 ], 7.11 [d, 1 H, J=8.1 Hz, H(8)], 7.57 [dd, 1 H, J=1.7 Hz, J=8.1 Hz, H(7)], 8.00 [d, 1 H, J=1.7 Hz, H(5)]; 13C NMR ppm 23.1 [ArSCH2CH2 ]26.2 [CH3C=O], 29.8 [(CH3)2C], 32.8 [(CH3)2C], 36.8 [ArSCH2CH2 ], 125.8, 126.2, 132.9, 139.4, 141.7, 196.7 [CH3C=O]. ##STR14##

Workup

  1. customequipped with a condenser and nitrogen inlet
  2. customthe two layers separated
  3. extractionThe aqueous layer was extracted with ether (3×50 mL)
  4. dry with materialdried (Na2SO4, 6 h)
  5. customAfter evaporation
  6. distillationdistilled

Sources & evidence

ORD record
ord-590e9c46e2314e3bb1da3a28be6d1909
Source dataset
uspto-grants-1989_05
Patent number
US04833254

Reaction notes

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