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Hydrogen iodide → 2-(4-Hydroxyphenyl)propionic acid

HRID 328162
Notes
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Reaction equation

HRID 328162 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([CH:11]([CH3:15])[C:12]([O-:14])=[O:13])[CH:7]=[CH:8][C:9]=1[OH:10])([O-])=O.COC1C=CC(C(C)C(O)=O)=CC=1.I>>[OH:10][C:9]1[CH:4]=[CH:5][C:6]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 24841Hydrogen iodideHCID 257576p-Methoxyphenylpropionic acidHCID 214441702-(3-Nitro-4-hydroxyphenyl)propionate

Product 1

HCID 1025262-(4-Hydroxyphenyl)propionic acid

Procedure

Also, the compounds (III) used for this invention, for example, 2-(3-nitro-4-hydroxyphenyl)propionate can be prepared by demethylating 2-(4-methoxyphenyl)propionic acid with hydroiodic acid and the like to obtain 2-(4-hydroxyphenyl)- propionic acid, by esterifying the above compound with an usual method to obtain, for example, methyl 2-(4-hydroxyphenyl)propionate and by nitrating the above compounds. Alternately, 2-(3-nitro-4-hydroxyphenyl)propionate can be prepared by nitrating the above 2-(4-hydroxyphenyl)propionic acid with an usual method and by esterificating the resultant compound. The above reactions can be applied to 4-hydroxyphenylacetate as well. The above reaction scheme is shown as follows: ##STR12## wherein R1 has the same meaning as above

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-76fb6a47486b484f804636832dc37f70
Source dataset
uspto-grants-1977_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04016193

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes