Benzyl Chloride → (+/-)-6-Benzyloxy-2,5,7,8-tetramethylchroman-2-carboxylic acid

HRID 268426Notes

Reaction equation

HRID 268426 reaction equation
OC1C(C)=C2C(=C(C)C=1C)OC(C)(C(O)=O)CC2.C(=O)([O-])[O-].[K+].[K+].C(Cl)C1C=CC=CC=1.[CH2:33]([O:40][C:41]1[C:42]([CH3:64])=[C:43]2[C:48](=[C:49]([CH3:52])[C:50]=1[CH3:51])[O:47][C:46]([CH3:63])([C:53]([O:55]CC1C=CC=CC=1)=[O:54])[CH2:45][CH2:44]2)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[OH-].[Na+]>O.CS(C)=O>[CH2:33]([O:40][C:41]1[C:42]([CH3:64])=[C:43]2[C:48](=[C:49]([CH3:52])[C:50]=1[CH3:51])[O:47][C:46]([CH3:63])([C:53]([OH:55])=[O:54])[CH2:45][CH2:44]2)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

8

Reactant 5

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 40634TroloxHCID 21483865(+/-)-Benzyl 6-benzyloxy-2,5,7,8-tetramethylchroman-2-carboxylate

Product 1

HCID 9905948(+/-)-6-Benzyloxy-2,5,7,8-tetramethylchroman-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a mixture of 0.5 g. of (±)- 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid and 1.3 g. of anhydrous potassium carbonate in 3 ml. of dimethylsulfoxide was added 1.0 g. of benzyl chloride. This mixture was stirred at 23° overnight to give a solution containing (±)-benzyl 6-benzyloxy-2,5,7,8-tetramethylchroman-2-carboxylate. To this solution was added 3 ml. of 1N sodium hydroxide solution and 2 ml. of dimethylsulfoxide and the resulting 2-phase solution was stirred at 100° for 16 hours. The mixture was cooled, diluted with H2O, washed with ether, acidified with 2N HCl, and extracted with ether. The ether solutions were washed with brine, dried over sodium sulfate and stripped of solvent. The residue was crystallized from ether-30°-60° petroleum ether to give (±)- 6-benzyloxy-2,5,7,8-tetramethylchroman-2-carboxylic acid as a white solid, m.p. 154.5°-155°.

Workup

  1. additionTo a mixture of 0.5 g
  2. customto give a solution
  3. additionTo this solution was added 3 ml
  4. temperatureThe mixture was cooled
  5. washwashed with ether
  6. extractionextracted with ether
  7. washThe ether solutions were washed with brine
  8. dry with materialdried over sodium sulfate
  9. customThe residue was crystallized from ether-30°-60° petroleum ether

Sources & evidence

ORD record
ord-afd66e5bccc9497dbfef3f602d37d6d1
Source dataset
uspto-grants-1976_03
Patent number
US03947473

Reaction notes

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