Benzenesulfonyl chloride → HCID 86595248, compound

HRID 1392896Notes

Reaction equation

HRID 1392896 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@H:7]([CH2:9][CH2:10][OH:11])[CH3:8])[CH3:3].C(N(CC)CC)C.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:19]1([S:25]([O:11][CH2:10][CH2:9][CH:7]([CH2:6][CH2:5][CH:4]=[C:2]([CH3:3])[CH3:1])[CH3:8])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 101977D-Citronellol

Product 1

HCID 86595248HCID 86595248, compoundYield 110%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of citronellol 6 (30.0 g, 192 mmol) in 400 mL CH2Cl2 was allowed to stir at 0° C. under N2 in a 1 L round bottom flask. Triethylamine (60 mL, 430 mmol) was added in one portion, followed by DMAP (2.0 g, 1.64 mmol). Finally, benzenesulfonyl chloride (30 mL, 240 mmol) was added dropwise via syringe. After the mixture was stirred for 2 h at 0° C., it was partitioned between petroleum ether and, sequentially, 3 M aqueous HCl, water, and brine. The organic layer was dried (Na2SO4) and the solvent was removed in vacuo at 30° C. Removal of residual solvent under high vacuum yielded citronellyl benzenesulfonate (62.4 g, 110% of theoretical) as a clear yellow oil, TLC Rf(10% MTBE/petroleum ether)=0.41. 1H NMR (CDCl3) (δ): 7.92 (m, 2H), 7.66 (m, 1H), 7.56 (m, 2H), 5.03 (m, 1H), 4.09 (m, 2H), 1.91 (m, 2H), 1.68 (m, 1H), 1.67 (s, 3H), 1.57 (s, 3H), 1.52 (m, 1H), 1.44 (m, 1H), 1.24 (m, 1H), 1.11 (m, 1H), 0.81 (d, J=6.49 Hz, 3H); 13C NMR (CDCl3) (δ): u: 136.1, 131.4, 69.2, 36.6, 35.5, 25.1; d: 133.6, 129.1, 127.7, 124.2, 28.7, 25.6, 18.9, 17.5; IR (cm−1): 2914, 1449, 1360, 1188, 944.

Workup

  1. stirringAfter the mixture was stirred for 2 h at 0° C.
  2. customit was partitioned between petroleum ether
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent was removed in vacuo at 30° C
  5. customRemoval of residual solvent under high vacuum

Sources & evidence

ORD record
ord-b09d3a76483e4f3bbbbbf2f04f33b016
Source dataset
uspto-grants-2008_03
Patent number
US07345035B2

Reaction notes

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