4-Toluenesulfonyl chloride → HCID 13133792, compound

HRID 2417596Notes

Reaction equation

HRID 2417596 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][C:4]=1[O:12][CH3:13].C(N(CC)CC)C.[S:21](Cl)([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22]>C(Cl)Cl.C(Cl)(Cl)Cl>[S:21]([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)([O:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:12][CH3:13])[CH:5]=1)(=[O:23])=[O:22]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 819113,4-Dimethoxyphenethyl alcohol

Product 1

HCID 13133792HCID 13133792, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,4-dimethoxyphenethanol (4.4 g) in methylene chloride (15 ml) containing triethylamine (2.7 g or 3.7 ml), was added gradually a solution of tosyl chloride (5.07 g) in methylene chloride (15 ml). The mixture was stirred at room temperature overnight. The mixture was diluted with chloroform and washed with water. The organic layer was separated, dried and evaporated to yield a crude product (11.7 g). The product was passed through a column of silica gel (250 g) and the eluates were evaporated to give 3,4-dimethoxyphenethyl tosylate (7.2 g): ir(CHCl3) 1600 and 1500 cm-1 ; and nmr(CDCl3) δ2.4 (s, 3H), 2.85 (m, 2H), 3.72 (s, 3H), 3.75 (s, 3H), 4.15 (t, 2H), 6.6 (m, 2H), 7.23 (m, 3H) and 7.64 (m, 2H).

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated
  5. customto yield a crude product (11.7 g)
  6. customthe eluates were evaporated

Sources & evidence

ORD record
ord-096d16ee702f4c409f0788180e767310
Source dataset
uspto-grants-1984_09
Patent number
US04469693

Reaction notes

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