Methanol → 2-(6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl)ethanol

HRID 1415249Notes

Reaction equation

HRID 1415249 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1([CH3:28])[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([CH3:27])[C:11]([CH3:26])=[C:12]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:13]=2[CH3:17])[O:8]1)(=O)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:19]([O:18][C:12]1[C:13]([CH3:17])=[C:14]2[C:9](=[C:10]([CH3:27])[C:11]=1[CH3:26])[O:8][C:7]([CH2:6][CH2:5][OH:4])([CH3:28])[CH2:16][CH2:15]2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 12085265HCID 12085265, compound

Product 1

HCID 109698772-(6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 0.5 g. of (±)-2-(2-acetoxyethyl)-6-benzyloxy-2,5,7,8-tetramethylchroman in 15 ml. of methanol was added a solution of 358 mg. of potassium carbonate in 1.5 ml. of water. The mixture was heated at reflux under N2 for 40 minutes, cooled, poured into water and extracted with methylene chloride. The methylene chloride solutions were washed with brine, dried over magnesium sulfate and stripped of solvent to give (±)-6-benzyloxy-2-(2-hydroxyethyl)-2,5,7,8-tetramethylchroman as an oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under N2 for 40 minutes
  3. temperaturecooled
  4. extractionextracted with methylene chloride
  5. washThe methylene chloride solutions were washed with brine
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-1bb6c7957c964c39a028be679ed1932c
Source dataset
uspto-grants-1977_01
Patent number
US04003919

Reaction notes

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