4-Toluenesulfonyl chloride → HCID 53918952, compound

HRID 839163Notes

Reaction equation

HRID 839163 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>N1C=CC=CC=1>[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=[CH:17][CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][CH:13]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 53858873HCID 53858873, compound

Product 1

HCID 53918952HCID 53918952, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

8-(4-Benzyloxyphenyl)-5-octenol (24 g.) was added in portions over a 15 minute period to a solution of 19.5 g. of p-toluenesulfonyl chloride in 600 ml. of dry pyridine at -10° C. The reaction mixture was stirred for one hour at -10° C., then poured into ice-water and stirred for 20 minutes. The mixture was extracted with chloroform, and the latter washed with aqueous hydrochloric acid, aqueous sodium hydroxide, dried and concentrated. The resulting 8-(4-benzyloxyphenyl)-5-octenyl p-toluenesulfonate was used directly in the next reaction without further purification.

Workup

  1. customat -10° C
  2. stirringstirred for 20 minutes
  3. extractionThe mixture was extracted with chloroform
  4. washthe latter washed with aqueous hydrochloric acid, aqueous sodium hydroxide
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting 8-(4-benzyloxyphenyl)-5-octenyl p-toluenesulfonate was used directly in the next reaction without further purification

Sources & evidence

ORD record
ord-1706a7283b174ceb934513e953f7f7d7
Source dataset
uspto-grants-1978_06
Patent number
US04093736

Reaction notes

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