Hydrogen Bromide → Benzenenonanoic acid, 4-hydroxy-

HRID 1723412Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:5][CH:4]=1.Br>>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 14555669HCID 14555669, compound

Product 1

HCID 10422225Benzenenonanoic acid, 4-hydroxy-

Procedure

In step 1 of this synthetic sequence, the ether group of 9(4-methoxyphenyl)nonanoic acid is cleaved with hydrogen bromide to give the alcohol, 9(4-hydroxyphenyl)nonanoic acid. In step 2, this acid is converted to its methyl ester. In step 3, the 9(4-hydroxyphenyl)nonanoic acid, methyl ester is alkylated (with n-butyl or n-hexyl bromide) and then hydrolyzed to give 9(4-alkoxyphenyl)nonanoic acids. In step 4, the acid is converted to the acid chloride, using thionyl chloride. In step 5, the acid chloride is condensed with a substituted or unsubstituted hydroxylamine to give the final product.

Sources & evidence

ORD record: ord-404a0aae218a4bb097437db4c93c960c
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04861798

Reaction notes

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