p-Toluenesulfonic acid → HCID 357800, compound

HRID 1390881Notes

Reaction equation

HRID 1390881 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 357781Ethyl 6-hydroxyhexanoate

Product 1

HCID 357800HCID 357800, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

66 g. (0.412 mol) of ethyl 6-hydroxyhexanoate [(prepared as described by S. R. Sandler and W. Karo, in `Organic Functional Group Preparation`, Academic Press, New York and London, vol. 1, page 262. (cf. G. B. Hatch and H. Adkins, J. Am. Chem. Soc., 59 1694 (1937))] were dissolved in 400 ml. of methylene chloride, and the mixture was reacted with 45 g. of dihydropyran and 1 g. of p-toluenesulphonic acid at 25° C. for 20 minutes. The reaction mixture was washed with an aqueous sodium bicarbonate solution, dried and concentrated. The residue was distilled in vacuo to obtain 77 g. of the title compound having the following physical characteristics:

Workup

  1. customKaro, in `Organic Functional Group Preparation`, Academic Press, New York and London
  2. dissolution(cf. G. B. Hatch and H. Adkins, J. Am. Chem. Soc., 59 1694 (1937))] were dissolved in 400 ml
  3. washThe reaction mixture was washed with an aqueous sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated
  6. distillationThe residue was distilled in vacuo
  7. customto obtain 77 g

Sources & evidence

ORD record
ord-48d2f406de09408b9fe08ee0b81a12c8
Source dataset
uspto-grants-1979_02
Patent number
US04140712

Reaction notes

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