Hydrochloric Acid → (2E)-3-(4-(methoxycarbonyl)phenyl)prop-2-enoic acid

HRID 909049Notes

Reaction equation

HRID 909049 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14]C(C)(C)C)=[O:13])=[CH:6][CH:5]=1.Cl.O1CCOCC1>>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:5]=[CH:6][C:7](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 42640359methyl (E)-4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)benzoate

Product 1

HCID 1472795(2E)-3-(4-(methoxycarbonyl)phenyl)prop-2-enoic acidYield 64.5%

Procedure

The crude 4-((E)-2-tert-butoxycarbonyl-vinyl)-benzoic acid methyl ester (1.00 g, 3.81 mmol) was then treated with 4N HCl in dioxane (Aldrich, 4 mL, 16.0 mmol) at rt for 2 hrs to give 4-((E)-2-carboxyvinyl)-benzoic acid methyl ester (0.43 g, 64.5%, 2 steps) after work up.

Sources & evidence

ORD record
ord-d0b0e3e617164e5dbf99451ce4615227
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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