p-Toluenesulfonic acid → HCID 54118752, compound

HRID 1981220Notes

Reaction equation

HRID 1981220 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5]([CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:7])=[O:6].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:28]1[CH:33]=[CH:32][CH2:31][CH2:30][CH2:29]1>ClCCl>[CH2:8]([S:5]([CH2:4][CH2:3][CH2:2][O:1][CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][O:28]1)(=[O:7])=[O:6])[CH:9]=[CH:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 54324610HCID 54324610, compound

Product 1

HCID 54118752HCID 54118752, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cinnamylthiopropionic acid, m.p. 87° C., was prepared from cinnamyl bromide and mercaptopropionic acid and oxidised by the method described in Example 23(a) to cinnamylsulphonylpropionic acid, m.p. 160° C. This acid was reduced by addition to a stirred suspension of lithium aluminium hydride (2 equivalents) in tetrahydrofuran at -20° to -25° C. and the product formed isolated by ethyl acetate extraction to give cinnamyl 3-hydroxypropyl sulphone, m.p. 86° C. A solution of cinnamyl 3-hydroxylpropyl sulphone, para-toluene sulphonic acid (catalytic) and dihydropyran (2 equivalents) in dichloromethane was allowed to stand at room temperature for 24 hours, evaporated, and recrystallised from diethyl ether to give the title compound, m.p. about 45° C.

Workup

  1. customevaporated
  2. customrecrystallised from diethyl ether

Sources & evidence

ORD record
ord-4aac49198a214157bfde3265f9eb55b6
Source dataset
uspto-grants-1985_04
Patent number
US04513005

Reaction notes

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