Methyl Gentisate → Methyl 5-(2-cyclohexylethoxy)-2-hydroxybenzoate

HRID 264351Notes

Reaction equation

HRID 264351 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1(C)C=CC(S(O[CH2:23][CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)(=O)=O)=CC=1>>[CH:25]1([CH2:24][CH2:23][O:12][C:9]2[CH:10]=[CH:11][C:2]([OH:1])=[C:3]([CH:8]=2)[C:4]([O:6][CH3:7])=[O:5])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 75077Methyl GentisateHCID 114260702-Cyclohexylethyl 4-methylbenzenesulfonate

Product 1

HCID 19036723Methyl 5-(2-cyclohexylethoxy)-2-hydroxybenzoateYield 43%

Procedure

Synthesis was carried out in the same manner as in Example 1, except for replacing methyl 2,4-dihydroxybenzoate with methyl 2,5-dihydroxybenzoate and replacing 2-ethylhexyl bromide with 2-cyclohexylethyl p-toluenesulfonate, to obtain methyl 5-(2-cyclohexylethoxy)-2-hydroxybenzoate represented by the following chemical formula (hereinafter referred to as compound 11) as a pale yellow solid in a yield of 43%. The analytical results are shown below. ##STR32##

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-dde65f479bc54da9b6f090eb6743d7ff
Source dataset
uspto-grants-1997_07
Patent number
US05646184

Reaction notes

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