Salicylic Acid → 3,5-Diisopropylsalicylic acid

HRID 1580317Notes

Reaction equation

HRID 1580317 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]>C(O)(C)C.S(=O)(=O)(O)O>[OH:4][C:3]1[C:5]([CH:2]([CH3:8])[CH3:1])=[CH:6][C:7]([CH:5]([CH3:6])[CH3:3])=[CH:8][C:2]=1[C:1]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 338Salicylic Acid

Product 1

HCID 305433,5-Diisopropylsalicylic acidYield 40%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 3776IsopropanolCatalyst

Procedure

Salicylic acid (0.67 m) was alkylated with 1.33 m isopropanol using 3.3 m concentrated sulphuric acid as catalyst at 70°C for six hours, to give 2-hydroxy-3,5-diisopropyl benzoic acid (m.p. 113°-116°C) in 40% yield. This was esterified to form the methyl ester and converted into its hydrazide using hydrate in aqueous ethanol. The hydrazide had a melting point of 111°-113°C and the following elemental analysis by weight:

Sources & evidence

ORD record
ord-9b3faf6a20984ec7a4950475a906c25e
Source dataset
uspto-grants-1976_01
Patent number
US03932505

Reaction notes

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