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

HRID 1182791Notes

Reaction equation

HRID 1182791 reaction equation
C(=O)([O-])[O-].[K+].[K+].S([O:12][CH3:13])(OC)(=O)=O.[CH2:14]([O:21][C:22]1[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24](O)[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[CH2:14]([O:21][C:22]1[C:31]([CH:32]([CH3:34])[CH3:33])=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([O:12][CH3:13])[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 58236452Methyl 4-benzyloxy-2-hydroxy-5-isopropylbenzoate

Product 1

HCID 58236472Methyl 4-benzyloxy-5-isopropyl-2-methoxybenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Anhydrous potassium carbonate (450 mg, 3.26 mmol) and dimethyl sulphate (0.25 ml, 2.64 mmol) were added to a suspension of methyl 4-benzyloxy-2-hydroxy-5-isopropylbenzoate (650 mg, 2.17 mmol) in acetonitrile (20 ml) and the mixture was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo and the residue acidified by the addition of 2M hydrochloric acid (20 ml). The organic material was extracted with ethyl acetate (2×30 ml) and the combined organic extracts were evaporated in vacuo to afford methyl 4-benzyloxy-5-isopropyl-2-methoxybenzoate (644 mg, 95%) as a pale yellow solid. 1H NMR (DMSO-d6) 7.56 (1H, s), 7.50 (2H, d), 7.43 (2H, t), 7.37 (1H, t), 6.80 (1H, s), 5.26 (2H, s), 3.83 (3H, s), 3.75 (3H, s), 3.19 (1H, m), 1.17 (6H, d). MS: [M+H]+ 315.

Workup

  1. temperatureat reflux for 16 hours
  2. customwas removed in vacuo
  3. additionthe residue acidified by the addition of 2M hydrochloric acid (20 ml)
  4. extractionThe organic material was extracted with ethyl acetate (2×30 ml)
  5. customthe combined organic extracts were evaporated in vacuo

Sources & evidence

ORD record
ord-d451771b254f477ba0319c26ca67db32
Source dataset
uspto-grants-2014_03
Patent number
US08664218B2

Reaction notes

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