2-Methyl-2-butene → 4-Benzyloxy-3,5-dimethylbenzoic acid

HRID 1177566Notes

Reaction equation

HRID 1177566 reaction equation
CC(=CC)C.Cl([O-])=O.[Na+].[CH2:10]([O:17][C:18]1[C:25]([CH3:26])=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=1[CH3:27])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.P([O-])(O)(O)=[O:29].[K+]>O.CC(O)(C)C>[CH2:10]([O:17][C:18]1[C:25]([CH3:26])=[CH:24][C:21]([C:22]([OH:29])=[O:23])=[CH:20][C:19]=1[CH3:27])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516951Monobasic potassium phosphate2×HCID 5635574-(Benzyloxy)-3,5-dimethylbenzaldehydeHCID 23668197Sodium Chlorite2×

Product 1

HCID 27339934-Benzyloxy-3,5-dimethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

2-Methyl-2-butene (3.31 mL, 31.2 mmol) and sodium chlorite (282 mg, 3.12 mmol) were sequentially added to a mixture of 4-(benzyloxy)-3,5-dimethyl-benzaldehyde (455 μl, 2.081 mmol) and potassium dihydrogen phosphate (425 mg, 3.12 mmol) in 1:1 water/t-BuOH (8.0 mL), and the resulting mixture was stirred at 25° C. for 4 h. Additional potassium dihydrogen phosphate (991 mg, 7.28 mmol) and sodium chlorite (659 mg, 7.28 mmol) were then sequentially added, and the resulting mixture was stirred at 25° C. for 15 h. The reaction mixture was subsequently partitioned between EtOAc (120 mL) and 0.02N aq. HCl (50 mL). The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% EtOAc/Hexanes) gave 4-(benzyloxy)-3,5-dimethylbenzoic acid as a white solid. MS (ESI) m/z: Calculated: 256.1; Observed: 257.2 (M++1).

Workup

  1. stirringthe resulting mixture was stirred at 25° C. for 15 h
  2. customThe reaction mixture was subsequently partitioned between EtOAc (120 mL) and 0.02N aq. HCl (50 mL)
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the residue (silica gel, 0-100% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-559f48dbb2ee4c45a05c808bc2f6b1ac
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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