2-Methyl-2-butene → 2-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid

HRID 505662Notes

Reaction equation

HRID 505662 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[CH:17]=[C:16]([O:18][CH2:19][O:20][CH3:21])[CH:15]=[C:14]([O:22][CH2:23][O:24][CH3:25])[C:11]=1[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(=CC)C.Cl([O-])=[O:32].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[CH2:1]([O:8][CH2:9][C:10]1[CH:17]=[C:16]([O:18][CH2:19][O:20][CH3:21])[CH:15]=[C:14]([O:22][CH2:23][O:24][CH3:25])[C:11]=1[C:12]([OH:32])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 216698172-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 687174092-(Benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acidYield 112.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

The above-obtained 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)benzaldehyde (0.80 g, 2.3 mmol) was dissolved in tert-butyl alcohol (20 mL) and the obtained solution was added with 2-methyl-2-butene (10 mL, 94 mmol), sodium chlorite (2.0 g, 22 mmol), sodium dihydrogen phosphate (2.0 g, 17 mmol) and water (5 mL), followed by stirring at a room temperature for 10 hours. The reaction mixture was extracted with chloroform 3 times. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate. Then the solvent was evaporated under reduced pressure to obtain 2-(benzyloxymethyl)-4,6-bis(methoxymethoxy)benzoic acid (0.94 g, 100%).

Workup

  1. extractionThe reaction mixture was extracted with chloroform 3 times
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThen the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-acfebf0766b54e6a9f1d4344baad0be6
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

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