Sulfuric Acid → Potassium 4-dodecylbenzenesulfonate

HRID 1854262Notes

Reaction equation

HRID 1854262 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:19][S:20](O)(=[O:22])=[O:21].[OH-].[K+:25]>>[CH2:7]([C:1]1[CH:6]=[CH:5][C:4]([S:20]([O-:22])(=[O:21])=[O:19])=[CH:3][CH:2]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[K+:25]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 31237Dodecylbenzene

Product 1

HCID 23672299Potassium 4-dodecylbenzenesulfonateYield 84%

Conditions

Temperature
90 °C

Procedure

A mixture of 1-phenyldodecane (7.5 g, 30.5 mmol) and concentrated H2SO4 (8.4 mL) was stirred vigorously at 90° C. for 1 h, cooled to room temperature, and then gradually poured with stirring into 10% aqueous KOH solution (175 mL). The resulting white precipitate was collected by filtration, washed with cold water (40 mL) and dried to give potassium 4-dodecylbenzene sulfonate (10.6 g, 29.1 mmol, 84%). This salt (10.0 g, 27.5 mmol) and POCl3 (4.2 g, 27.4 mmol) were stirred at room temperature and gradually heated to 170° C. The hot reaction mixture was poured into cold water and extracted with CHCl2. The organic layer was washed with water, dried over anhydrous Na2SO4, and filtered. Evaporation of the volatiles yielded p-dodecylbenzenesulfonyl chloride as a pale yellow liquid (9.2 g, 97%) which eventually became crystalline, mp 33° C.; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J=6.5), 1.20-1.38 (m, 18H), 1.60-1.68 (m, 2H), 2.72 (t, 2H, J=7.5 Hz), 7.40 (d, 2H, J=8.4 Hz), 7.79 (d, 2H, J=8.4 Hz); 13C NMR (75 MHz, CDCl3) δ 14.1, 22.6, 29.1, 29.3, 29.3, 29.5, 29.6, 30.9, 31.9, 36.0, 127.0, 129.6, 141.7, 151.6.

Workup

  1. temperaturecooled to room temperature
  2. additiongradually poured
  3. filtrationThe resulting white precipitate was collected by filtration
  4. washwashed with cold water (40 mL)
  5. customdried

Sources & evidence

ORD record
ord-130d5171a5b141a286c5aafd101362dc
Source dataset
uspto-grants-2015_02
Patent number
US08962663B2

Reaction notes

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