1-Chloro-4-(chloromethyl)benzene → HCID 86676534, 화합물

HRID 73505노트

반응식

HRID 73505 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[CH:14]=[O:15].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH:14]=[O:15])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 112306483-Hydroxy-4-[(4-methoxyphenyl)methoxy]benzaldehyde

생성물 1

HCID 86676534HCID 86676534, 화합물수율 73.6%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 180Acetone용매

실험 절차

A solution of 4-chlorobenzyl chloride (67.9 g), 3-hydroxy-4-(4-methoxy-benzyloxy)-benzaldehyde (40) (99 g) and tetrabutylammonium iodide (14.1 g) was heated at reflux in acetone (0.4 L) over solid potassium carbonate (39.1 g) for 3 hours. Excess acetone was removed by rotary evaporation under reduced pressure and the resulting residue partitioned between ethyl acetate and dilute hydrochloric acid (0.5 N). The organic layer was washed with water and brine and then dried over magnesium sulphate. Ethyl acetate was removed by rotary evaporation under reduced pressure to afford the crude product. The crude oil was triturated with a 50/50 mixture of diethyl ether and hexane accompanied by vigorous stirring to afford the product as a colourless solid (108 g, 73% yield, retention time 3.70 mins, poor ionization, ES− m/z 538.05). 1H NMR (400 MHz, CDCl3) δ 9.84 (s, 1H), 7.51-7.43 (m, 2H), 7.42-7.32 (m, 6H), 7.07 (d, J=8.1 Hz, 1H), 6.97-6.89 (m, 2H), 5.19 (s, 2H), 5.17 (s, 2H), 3.85 (s, 3H).

후처리

  1. customExcess acetone was removed by rotary evaporation under reduced pressure
  2. customthe resulting residue partitioned between ethyl acetate and dilute hydrochloric acid (0.5 N)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customEthyl acetate was removed by rotary evaporation under reduced pressure
  6. customto afford the crude product
  7. customThe crude oil was triturated with a 50/50 mixture of diethyl ether and hexane

출처 및 근거

ORD 기록
ord-ce12807a553c4e0aa6516372fa81cd19
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829184B2

반응 노트

불러오는 중…