Dichloromethane → 4-Dodecyloxybenzyl alcohol

HRID 2241852

반응식

HRID 2241852 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24](OC)=[O:25])=[CH:22][CH:21]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)Cl>C1COCC1>[CH2:7]([O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][OH:25])=[CH:28][CH:29]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 592397Methyl 4-(dodecyloxy)benzoateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 144776284-Dodecyloxybenzyl alcohol수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a 0° C. slurry of LAH (13.0 g, 343 mmol) in dry THF (400 mL) was added slowly methyl 4-dodecyloxybenzoate (100 g, 312 mmol) in dry THF (350 mL) over 1.5 hours. Upon addition, the mixture was stirred at room temperature for one hour, after which TLC (CH2Cl2) showed completion. Reaction was cooled to 0° C. and quenched by successive addition of H2O (13 mL), 15% NaOH (13 mL), and H2O (39 mL), and stirring continued until H2 evolution ceased. Reaction mixture was then filtered and the lithium salts rinsed generously with CH2Cl2. The filtrate was dried over MgSO4 and concentrated to give the title benzyl alcohol (80 g, 88%), which was taken to the next step without further purification.

후처리

  1. additionUpon addition
  2. customReaction
  3. temperaturewas cooled to 0° C.
  4. customquenched by successive addition of H2O (13 mL), 15% NaOH (13 mL), and H2O (39 mL)
  5. stirringstirring
  6. customReaction mixture
  7. filtrationwas then filtered
  8. washthe lithium salts rinsed generously with CH2Cl2
  9. dry with materialThe filtrate was dried over MgSO4
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bd6f67588d84496dbd22e926be13980a
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671033B2

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