Water → HCID 25056515, compound

HRID 1258990Notes

Reaction equation

HRID 1258990 reaction equation
[H-].[Na+].[CH3:3][C:4](=[CH2:7])[CH2:5][OH:6].Cl[CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14].O>O1CCCC1>[CH3:7][C:4](=[CH2:3])[CH2:5][O:6][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 10557Methallyl alcoholHCID 24758Sodium hydrideHCID 2417523-(Chloromethyl)benzoic acid

Product 1

HCID 25056515HCID 25056515, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the suspension of Sodium Hydride (1.516 g, 95%, 60 mmol) in tetrahydrofuran (150 ml), 2-Methyl-prop-2-en-1-ol (4.323 g, 4.1 ml, 60 mmol) was added. After the reaction mixture was refluxed for 30 min, 3-Chloromethyl-benzoic acid (4.10 g, 24 mmol) was added and the reaction was kept to reflux for additional 10 h. After cooling down, water (100 ml) was added and the tetrahydrofuran was removed under vacuum. This resulting aqueous solution was adjusted with 6N HCl to pH 2 at 5° C., and the mixture was extracted with Et2O (50 ml×3). The organic phase was combined and washed with water (10 ml×2) respectively. The ether extract was dried with anhydrous sodium sulfate and then concentrated to give 3-(2-Methyl-allyloxymethyl)-benzoic acid as colorless oil (4.25 g, 85.9%). 1H-NMR (400 MHz, d6-DMSO): 7.90 (m, 1 arom.H); 7.85 (m, 1 arom.H); 7.55 (m, 1 arom.H); 7.45 (m, 1 arom.H); 4.96, 4.88 (2 s-like; C═CH2); 4.50 (s, —OCH2—C6H4); 3.90 (s, CH2O); 1.69 (s, CH3). 13C-NMR (100 MHz, d6-DMSO): 167.22 (—C═O); 142.03; 139.00; 131.72; 130.78; 128.56; 128.31; 128.07; 111.71; 73.41; 70.58; 19.30.

Workup

  1. additionwas added
  2. temperatureAfter the reaction mixture was refluxed for 30 min
  3. temperatureto reflux for additional 10 h
  4. temperatureAfter cooling down
  5. customthe tetrahydrofuran was removed under vacuum
  6. customwas adjusted with 6N HCl to pH 2 at 5° C.
  7. extractionthe mixture was extracted with Et2O (50 ml×3)
  8. washwashed with water (10 ml×2) respectively
  9. extractionThe ether extract
  10. dry with materialwas dried with anhydrous sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ecc43e0cac7a45e59b6c763dc07575fa
Source dataset
uspto-grants-2013_06
Patent number
US08466199B2

Reaction notes

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