Dimethyl Sulfate → Methyl 2-hydroxy-5-isopropyl-4-methoxybenzoate

HRID 1182794Notes

Reaction equation

HRID 1182794 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(#N)C>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:16])[C:9]([CH:13]([CH3:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 59167875Methyl 2,4-dihydroxy-5-(propan-2-yl)benzoate

Product 1

HCID 58236455Methyl 2-hydroxy-5-isopropyl-4-methoxybenzoateYield 98.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 2,4-dihydroxy-5-isopropylbenzoate (420 mg, 2.0 mmol) and anhydrous potassium carbonate (331 mg, 2.4 mmol) in acetonitrile (10 ml) was treated with dimethyl sulphate (0.2 ml, 2.1 mmol) and the mixture was stirred at room temperature for 16 hours. The solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (10 ml). The solid material was collected by suction filtration, rinsed with water (2×10 ml) and sucked dry under reduced pressure to afford methyl 2-hydroxy-5-isopropyl-4-methoxybenzoate (440 mg, 98%) as a colourless solid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue acidified by the addition of 2M hydrochloric acid (10 ml)
  3. filtrationThe solid material was collected by suction filtration
  4. washrinsed with water (2×10 ml)
  5. customsucked dry under reduced pressure

Sources & evidence

ORD record
ord-a31165460b974c1f8bea84b024b2f26a
Source dataset
uspto-grants-2014_03
Patent number
US08664218B2

Reaction notes

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