Allyl bromide → Methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate

HRID 389957Notes

Reaction equation

HRID 389957 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][O:14][CH3:15])[C:9]([CH:16]([CH3:18])[CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>C(#N)C>[CH2:27]([O:1][C:2]1[CH:11]=[C:10]([O:12][CH2:13][O:14][CH3:15])[C:9]([CH:16]([CH3:18])[CH3:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH:26]=[CH2:25]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 58236463Methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate

Product 1

HCID 58236458Methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate (995 mg, 3.92 mmol) and anhydrous potassium carbonate (650 mg, 4.71 mmol) in acetonitrile (25 ml) was treated with allyl bromide (0.356 ml, 4.11 mmol) and the mixture was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo, water (30 ml) was added and the organic material was extracted with dichloromethane (2×30 ml). The combined organic extracts were evaporated to dryness in vacuo to afford methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate (1125 mg, 97%) as pale yellow oil. 1H NMR (DMSO-d6) 7.58 (1H, s), 6.78 (1H, s), 6.03 (1H, m), 5.52 (1H, dm), 5.33 (2H, s), 5.28 (1H, dm), 4.61 (2H, m), 3.78 (3H, s), 3.42 (3H, s), 3.19 (1H, m), 1.18 (6H, d). MS: [M+Na]+ 317.

Workup

  1. temperatureat reflux for 16 hours
  2. customwas removed in vacuo, water (30 ml)
  3. additionwas added
  4. extractionthe organic material was extracted with dichloromethane (2×30 ml)
  5. customThe combined organic extracts were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-bab5057a69834a64820784c0abdf5497
Source dataset
uspto-grants-2013_02
Patent number
US08383619B2

Reaction notes

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