Potassium Carbonate → (2,2-Diethoxyethyl)(3-methoxyphenyl)sulfane

HRID 979555Notes

Reaction equation

HRID 979555 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Br)[CH3:2].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([SH:18])[CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][S:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH3:10])[CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 849893-Methoxybenzenethiol

Product 1

HCID 13642516(2,2-Diethoxyethyl)(3-methoxyphenyl)sulfaneYield 97.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Bromoacetaldehyde diethyl acetal (16.5 ml, 0.11 mol) was added dropwise to a mixture of m-methoxybenzenethiol (15.0 ml, 0.12 mol) and K2CO3 (16.6 g, 0.12 mol) in acetone (150 ml) at room temperature. The reaction mixture was stirred for 16 hours and then filtered. The solid was washed with acetone, and the combined filtrate and washes were concentrated in vacuo. The residue was diluted with H2O and extracted with Et2O. The Et2O extracts were washed with 0.5 M KOH, H2O, and brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 27.4 g of 1-[(2,2-diethoxy)ethylthio]-3-methoxybenzene as a dark yellow oil. 'H NMR, δ :(CDCl3):1.18 (6H, t, --OCHHD 2CH3); 3.13 (2H, d, --SCH--); 3.43-3.73 (4H, m, --OC/H/ 2CH3); 3.77 (3H, s, --OCH 3); 4.67 (1H, t, --SCH2C/H/ --); 6.60-7.27 (4H, m, aromatics).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with acetone
  3. concentrationthe combined filtrate and washes were concentrated in vacuo
  4. additionThe residue was diluted with H2O
  5. extractionextracted with Et2O
  6. washThe Et2O extracts were washed with 0.5 M KOH, H2O, and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69f1a76d35ea4ed3b16c6cb39b1c8c78
Source dataset
uspto-grants-1987_05
Patent number
US04668697

Reaction notes

Loading…