Acetic Anhydride → 6-(4-Formyl-2-methoxyphenoxy)hexyl acetate

HRID 987392노트

반응식

HRID 987392 반응식
[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[C:5]([O:17][CH3:18])[CH:4]=1)=[O:2].[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[C:19]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:15]=[CH:16][C:3]([CH:1]=[O:2])=[CH:4][C:5]=1[O:17][CH3:18])(=[O:21])[CH3:20]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 180087914-[(6-Hydroxyhexyl)oxy]-3-methoxybenzaldehyde

생성물 1

HCID 180087926-(4-Formyl-2-methoxyphenoxy)hexyl acetate수율 99%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A flame-dried, 250 mL round bottom flask was charged, under argon, with 2 (10 g, 39.6 mmol) and this was dissolved in 50 mL of anhydrous pyridine and the flask was protected from light. To this solution was added acetic anhydride (9.3 mL, 98.8 mmol) dropwise at a rate of 0.5 mL/minute. The solution was stirred at room temperature for 30 minutes at which time all of the starting material had been consumed. The solvent was evaporated with reduced pressure and then toluene was added to remove excess pyridine. Evaporation of the solvent in vacuo gave 11.5 g (99%) of 3 as an off-white solid. Rf=0.74 (33% ethyl acetate/hexane). Mp 74.0-75.0° C. 1H NMR (400 MHz, DMSO-d6): δ9.83 (s, 1), 7.53 (dd, J=1.6 Hz, 8.4 Hz, 1), 7.39 (d, J=2.0 Hz, 1),), 7.17 (d, J=8.4 Hz, 1), 4.07 (t, J=6.4 Hz, 2), 4.00 (pt, J=6.4 Hz, 6.8 Hz, 2), 3.83 (s, 3), 2.00 (s, 3) 1.74 (m, 2), 1.58 (m, 2), 1.4-1.35 (m, 4) ppm.

후처리

  1. customhad been consumed
  2. customThe solvent was evaporated with reduced pressure
  3. additiontoluene was added
  4. customto remove excess pyridine
  5. customEvaporation of the solvent in vacuo

출처 및 근거

ORD 기록
ord-16b88a70e4494bfd8409286495270ba4
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06632641B1

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