Hydrochloric Acid → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzyl alcohol

HRID 982056노트

반응식

HRID 982056 반응식
[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>CCOCC.O>[CH3:1][C:2]1([CH3:25])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:24]=[CH:23][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10314719Agn-190205HCID 21226445Aluminium lithium hydride

생성물 1

HCID 539501414-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzyl alcohol수율 48%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

A suspension of 15.8 g (48 millimoles) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzoic acid (Example 6) in 160 ml of absolute ether was added dropwise to a suspension of 1.9 g (49 millimoles) of lithium aluminum hydride in 150 ml of absolute ether. Thereafter, the mixture was stirred under reflux for 3 hours, after which 50 ml of ethyl acetate, 200 ml of water and 150 ml of 2N HCl were added dropwise in succession, and the phases were separated. The aqueous phase was extracted once again with ether, and the combined ether extracts were washed with water, dried over Na2SO4 and evaporated down. The oil which remained (17 g) was stirred with heptane, and the resulting crystals were filtered off under suction and dried. 7.2 g (48%) of the title compound of melting point 115°-117° C. were obtained in this manner.

후처리

  1. temperatureunder reflux for 3 hours
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted once again with ether
  4. washthe combined ether extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated down
  7. stirringwas stirred with heptane
  8. filtrationthe resulting crystals were filtered off under suction
  9. customdried

출처 및 근거

ORD 기록
ord-f5af234b3b13476db2939ebe82cc1982
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994489

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