Ethanol → (+/-)-6-Benzyloxy-2,5,7,8-tetramethylchroman2-acetic acid

HRID 328868Notes

Reaction equation

HRID 328868 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:25])=[C:11]2[C:16](=[C:17]([CH3:20])[C:18]=1[CH3:19])[O:15][C:14]([CH3:24])([CH2:21][CH:22]=[O:23])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([OH:28])C.[OH-].[Na+]>[N+]([O-])([O-])=O.[Ag+].O>[CH2:1]([O:8][C:9]1[C:10]([CH3:25])=[C:11]2[C:16](=[C:17]([CH3:20])[C:18]=1[CH3:19])[O:15][C:14]([CH3:24])([CH2:21][C:22]([OH:28])=[O:23])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13422213(6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetaldehyde

Product 1

HCID 14368743(+/-)-6-Benzyloxy-2,5,7,8-tetramethylchroman2-acetic acid

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

To a solution of 6.09 g. of (±)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-acetaldehyde in 280 ml. of ethanol was added a solution of 3.57 g. of silver nitrate in 42 ml. of H2O followed, dropwise over 0.5 hour, by a solution of 3.49 g. of sodium hydroxide in 100 ml. of H2O. The mixture was stirred at 23° for 2.0 hours, filtered, concentrated in vacuo, diluted with H2O, and extracted with ether. The aqueous solution was acidified with 1 N HCl and again extracted with ether. These latter extracts were washed with brine, dried over magnesium sulfate and stripped of solvents to give (±)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-acetic acid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. additiondiluted with H2O
  4. extractionextracted with ether
  5. extractionagain extracted with ether
  6. washThese latter extracts were washed with brine
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-808fec93cc0e41eebc6752c9344ed00f
Source dataset
uspto-grants-1977_04
Patent number
US04018799

Reaction notes

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