Water → Methyl 3-hydroxy-5-isopropoxybenzoate

HRID 2113813Notes

Reaction equation

HRID 2113813 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([CH3:10])[CH3:9].[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[C:16]([OH:21])[CH:15]=1.O>CN(C)C=O.C(OC(=O)C)C>[CH3:11][O:12][C:13](=[O:22])[C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[C:18]([O:20][CH:8]([CH3:10])[CH3:9])[CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 23072925Methyl 3-hydroxy-5-isopropoxybenzoateYield 30,042.801%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

After adding 41.0 g (0.30 mmol) of potassium carbonate and 23.8 g (0.19 mmol) of 2-bromopropane to a solution of 25.0 g (0.15 mol) of 3,5-dihydroxybenzoic acid methyl ester in N,N-dimethylformamide (250 ml), the reaction mixture was stirred at 80° C. for 4 hours. Water was added to the reaction mixture, extraction was performed with acetic acid ethyl ester, and then the organic layer was washed with brine, dried and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1) to obtain 12.0 g of 5-hydroxy-3-isopropoxybenzoic acid methyl ester (yield: 38%) as a colorless oil.

Workup

  1. washthe organic layer was washed with brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1)

Sources & evidence

ORD record
ord-75240f6ae57d485f8feb8edd7a29b7c2
Source dataset
uspto-grants-2008_10
Patent number
US07432287B2

Reaction notes

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