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

HRID 268426

반응식

HRID 268426 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-afd66e5bccc9497dbfef3f602d37d6d1
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03947473

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