Naphthalene → 3-Decyn-5-ol

HRID 1283517노트

반응식

HRID 1283517 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Li].[Li].C1C2C(=CC=CC=2)C=CC=1.C=CC=C.C(=[O:33])CCCCC>O1CCCC1>[CH3:1][CH2:2][C:3]#[C:4][CH:5]([OH:33])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

참가 물질

7

반응물 5

HCID 931NaphthaleneHCID 6184HexanalHCID 78451,3-ButadieneHCID 3028194LithiumHCID 57466756Lithium Naphthalene

생성물 1

HCID 215184413-Decyn-5-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
55 °C

실험 절차

Following the procedure of Example 1, but with a pressure equalizing dropping funnel in place of the gas addition tube, 100 g. of naphthalene (0.77 moles) were added to 7.3 g. of lithium metal powder (1.05 moles) in 100 ml. tetrahydrofuran forming a dark green-brown lithium-naphthalene adduct over a period of about 30 minutes. 168 g. of the gaseous hydrocarbon mixture of Example 1 dissolved in 800 ml. tetrahydrofuran were added to the flask over a two hour period while maintaining the slurry at a temperature of about 55°C. Near the end of the addition, the slurry turned to an olive green color and became light brown after stirring for an additional hour. An aliquot of the resultant product was reacted with 1-hexanal producing 3-decyn-5-ol which, by gas chromotograph analysis, establishes a yield of butynyllithium in excess of 90%, based on lithium.

후처리

  1. additionin place of the gas addition tube, 100 g
  2. additionNear the end of the addition

출처 및 근거

ORD 기록
ord-d74eaf3fba7c4b948c3ead48196f2dd8
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03975453

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