p-Toluenesulfonic acid → methyl delta-hydroxy-2-(5-hydroxy-1E,3E-tridecadienyl)benzenepentanoate

HRID 1722342Notes

Reaction equation

[OH:1][CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:16]=[CH:17]/[CH:18]=[CH:19]/[CH:20]([O:29]C1CCCCO1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:1][CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:16]=[CH:17]/[CH:18]=[CH:19]/[CH:20]([OH:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 55 °C

Procedure

To 3ml of methanol is added 0.1g (0.21 mmol) of the titled product of Example 12 and 10mg of p-toluenesulfonic acid. The reaction mixture is heated to 55°C. for 3 hours. The solvent was removed under reduced pressure and the residue was flash chromatographed on silica gel column. Elution with 2:1 diethyl ether hexane produced 3 bands. The third band contained 0.30g of the titled products which was collected as fractions 8-18.

Workup

customThe solvent was removed under reduced pressure
customchromatographed on silica gel column
washElution with 2:1 diethyl ether hexane
customproduced 3 bands
customwas collected as fractions 8-18

Sources & evidence

ORD record: ord-334a174b414f4971bd9859540b6c9e33
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04855324

Reaction notes

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