4-Toluenesulfonyl chloride → HCID 53951603, compound

HRID 1493111Notes

Reaction equation

HRID 1493111 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C1(C)C=CC(S(O[CH2:22][CH2:23][CH:24]=[C:25]([CH3:34])[CH2:26][CH:27]([OH:33])[CH:28]=[CH:29][C:30]([CH3:32])=[CH2:31])(=O)=O)=CC=1>N1C=CC=CC=1>[CH3:34][C:25]1[CH2:26][CH:27]([CH:28]=[CH:29][C:30]([CH3:32])=[CH2:31])[O:33][CH2:22][CH2:23][CH:24]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 53826896HCID 53826896, compound

Product 1

HCID 53951603HCID 53951603, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cool solution of the diol prepared according to g) (2.0 g, 10.2 mmole) in pyridine (22 ml) was added p-toluenesulfonyl chloride (2.13 g, 11.2 mmole) in small portions and over 30 min. The mixture was stirred at 0° for 30 min and then stored overnight at 3°. The usual extraction with ether and treatment of the organic phase gave 2.85 g of a crude product which, on thin layer chromatographic analysis, showed two components. The further purification of this product by MPLC [LOBAR® column (origin: Merck), mixture of hexane-ethyl acetate as elution agent] gave 2.20 g (yield: 61.6%) of the desired product, i.e. 6-hydroxy-4,9-dimethyl-3,7,9-decatrienyl p-toluenesulfonate, and 220 mg of an unidentified by-product.

Workup

  1. customprepared
  2. waitstored overnight at 3°
  3. extractionThe usual extraction with ether and treatment of the organic phase
  4. customgave 2.85 g of a crude product which
  5. customThe further purification of this product
  6. additionby MPLC [LOBAR® column (origin: Merck), mixture of hexane-ethyl acetate as elution agent]

Sources & evidence

ORD record
ord-8ff6a1f6601046a1bb12f4e82bc3da3e
Source dataset
uspto-grants-1991_06
Patent number
US05021402

Reaction notes

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