(2E,4E)-hexa-2,4-dienoyl chloride → 6-O-Palmitoyl-2-O-sorboyl-L-ascorbic Acid

HRID 1857049

반응식

HRID 1857049 반응식
[C:1]([O:18][CH2:19][C@H:20]([OH:29])[C@H:21]1[O:26][C:24](=[O:25])[C:23]([OH:27])=[C:22]1[OH:28])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:30](Cl)(=[O:36])/[CH:31]=[CH:32]/[CH:33]=[CH:34]/[CH3:35]>N1C=CC=CC=1.ClCCl>[C:1]([O:18][CH2:19][C@H:20]([OH:29])[C@H:21]1[O:26][C:24](=[O:25])[C:23]([O:27][C:30](=[O:36])/[CH:31]=[CH:32]/[CH:33]=[CH:34]/[CH3:35])=[C:22]1[OH:28])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

참가 물질

5

반응물 2

HCID 5368941(2E,4E)-hexa-2,4-dienoyl chlorideHCID 54680660Ascorbyl Palmitate

생성물 1

HCID 1317221496-O-Palmitoyl-2-O-sorboyl-L-ascorbic Acid

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

50 g (120 mmol; 1 eq.) of 6-O-palmitoyl-L-ascorbic acid were dissolved in 400 ml of pyridine in a 1 l 4-necked flask. 23.40 g (130 mmol; 1.1 eq.) of sorboyl chloride, dissolved in 30 ml of dichloromethane, were slowly added dropwise at an internal temperature of -15° C. Care was taken here that the internal temperature did not exceed -10° C. The mixture was brought to room temperature and additionally stirred for 2 hours. The reaction solution was concentrated on a rotary evaporator and then codistilled with toluene. The residue was taken up in a little dichloromethane and extracted with 1 M HCl. The organic phase was concentrated somewhat and treated with an excess of n-hexane. A white precipitate was deposited, which was dried in an oil pump vacuum.

후처리

  1. additionwere slowly added dropwise at an internal temperature of -15° C
  2. customdid not exceed -10° C
  3. customwas brought to room temperature
  4. concentrationThe reaction solution was concentrated on a rotary evaporator
  5. extractionextracted with 1 M HCl
  6. concentrationThe organic phase was concentrated somewhat
  7. additiontreated with an excess of n-hexane
  8. customwhich was dried in an oil pump vacuum

출처 및 근거

ORD 기록
ord-c4c4381317124191bc8665151ec29b64
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06143906

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