4-Hydroxybenzyl Alcohol → 9-Decenoxybenzyl alcohol

HRID 29733

반응식

HRID 29733 반응식
O[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[OH-:10].[Na+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22]>C(O)C>[CH2:13]([O:7][CH:6]([OH:10])[C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22]

참가 물질

5

반응물 3

HCID 1254-Hydroxybenzyl Alcohol2회HCID 14798Sodium HydroxideHCID 54338410-Bromo-1-decene2회

생성물 1

HCID 692158849-Decenoxybenzyl alcohol수율 64.3%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
65 °C

실험 절차

First, 12.80 g (0.10 M) of 4-hydroxybenzyl alcohol (compound (6)) was dissolved in 190 mL of ethanol, and 4.0 g (0.10 M) of sodium hydroxide was added thereto. The resulting mixture was heated to 65° C. After heating, 24.14 g (0.11 M) of 10-bromo-1-decene (compound (22)) prepared in Synthetic example 1-1 was added dropwise, and the resulting mixture was aged at a mixture temperature of 760° C. for 6 hours. Next, the generated salt was removed by decantation, and the reaction solution was concentrated. After concentration, the resulting solution was diluted with 350 mL of diethyl ether and washed twice with 100 mL of deionized water. After washing, the organic layer was concentrated to produce crude crystals. The crude crystals were recrystallized twice from 25 mL of hexane. The recrystallized crystals were washed with hexane and dried. Thereby, 16.88 g of 9-decenoxybenzyl alcohol (compound (23)) was produced (yield: 64.3%).

후처리

  1. temperatureAfter heating
  2. additionwas added dropwise
  3. customNext, the generated salt was removed by decantation
  4. concentrationthe reaction solution was concentrated
  5. concentrationAfter concentration
  6. additionthe resulting solution was diluted with 350 mL of diethyl ether
  7. washwashed twice with 100 mL of deionized water
  8. washAfter washing
  9. concentrationthe organic layer was concentrated
  10. customto produce crude crystals
  11. customThe crude crystals were recrystallized twice from 25 mL of hexane
  12. washThe recrystallized crystals were washed with hexane
  13. customdried

출처 및 근거

ORD 기록
ord-3b38e2caeee64c1a91defc23d4609f24
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07422702B2

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