p-Toluenesulfonic acid → HCID 86748924, compound

HRID 1757210Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of (E)-6-(1,3-dihydro-6-ethyl-4-hydroxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid in methanol (200 ml) was treated with p-toluenesulfonic acid (0.8 g) and stirred at 25° C. for 16 hours. The reaction mixture was cooled to 0° C. Methyl (E)-6-(1,3-dihydro-6-ethyl-4-hydroxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate, m.p. 116.5°-117.6, was collected by filtration.

Workup

temperatureThe reaction mixture was cooled to 0° C
filtrationMethyl (E)-6-(1,3-dihydro-6-ethyl-4-hydroxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate, m.p. 116.5°-117.6, was collected by filtration

Sources & evidence

ORD record: ord-a801c855bf3a4b52b5407bf4c17ad147
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05444072

Reaction notes

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