Hydrochloric Acid → 4-Pentyl-3-cyclohexen-1-methanol toluenesulfonate

HRID 326959Notes

Reaction equation

HRID 326959 reaction equation
[CH2:1]([C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[C:14]1(C)[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.Cl.N1C=CC=C[CH:27]=1>>[C:16]1([CH3:27])[C:17]([S:20]([O:13][CH2:12][CH:9]2[CH2:10][CH2:11][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:7][CH2:8]2)(=[O:21])=[O:22])=[CH:18][CH:19]=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 197340354-Pentyl-3-cyclohexen-1-methanol

Product 1

HCID 197340424-Pentyl-3-cyclohexen-1-methanol toluenesulfonate

Procedure

To a solution of 4-pentyl-3-cyclohexen-1-methanol (3.0 g) in pyridine (3.3 ml) at 0° C. was added p-toluenesulfonyl chloride (3.3 g). The reaction was stirred in an ice bath for 2 hours, and then stored at -20 ° C. for a further 16 hours. The reaction mixture was then poured into 2 M HCl (75 ml) and extracted with ethyl acetate. The combined organic layers were extracted with saturated sodium chloride and dried over sodium sulfate. The solvent was removed in vacuo to produce 4-pentyl-3-cyclohexen-1-methanol toluenesulfonate.

Workup

  1. waitstored at -20 ° C. for a further 16 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe combined organic layers were extracted with saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ae801b14e8a045ceb9b70ec58a74af77
Source dataset
uspto-grants-1993_12
Patent number
US05271864

Reaction notes

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