Retinol, acetate → Unii-61911N8D6W

HRID 230739

반응식

HRID 230739 반응식
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:24])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:23])=[CH:17]/[CH2:18][O:19][C:20]([CH3:22])=[O:21].[C:25](O)(=O)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40]CC>C1(C)C=CC=CC=1>[CH3:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:22][C:20]([O:19][CH2:18]/[CH:17]=[C:16](\[CH:15]=[CH:14]\[CH:13]=[C:12](/[CH:11]=[CH:10]/[C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])\[CH3:24])/[CH3:23])=[O:21]

참가 물질

4

반응물 2

HCID 638034Retinol, acetateHCID 5280450Linoleic Acid

생성물 1

HCID 6440169Unii-61911N8D6W

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Retinyl acetate (22.0 g; 80% in oil; 53.6 mmol) and linoleic acid (Pamolyn 200; 15.0 g; 53.6 mmol; 1.0 equiv) were dissolved in 160 mL of toluene in a 500 mL flask. A dip tube in the flask was connected through a peristaltic pump to a column containing 6.0 g of Novozyme 435 which was connected in sequence to a second column containing 6.0 g of dried Amberlyst A-21. A tube from this second column returned to the original flask. The pump was started (flow rate 6 mL/min) sending the reaction mixture through the two columns and then back to the pot. After 6 h conversion had reached 71%, and the pump was stopped and the Amberlyst resin was regenerated by removing the column and washing the contents with 100 mL of 10% triethylamine in toluene (with 100 mL of toluene chaser). The apparatus was reassembled and the pump re-started. After 3 more hours conversion had reached 75% and the pump was stopped. Approximately 50% of the contents of the pot (80 mL) was removed and a mixture of 11.0 g of 80% retinyl acetate and 7.5 g of linoleic acid in 80 mL of toluene was added to the pot to serve as a first reactant replenishment. The Amberlyst resin was regenerated as above, the apparatus reassembled, and the pump started. After 9 h 73.6% conversion had been achieved and the pump was stopped. Approximately 50% of the contents of the pot (80 mL) was removed and a mixture of 11.0 g of 80% retinyl acetate and 7.5 g of linoleic acid in 80 mL of toluene was added to the pot to serve as a second replenishment. The Amberlyst resin was regenerated as above, the apparatus reassembled, and the pump started. After 12 h 75.0% conversion had been achieved and the reaction was stopped.

후처리

  1. customA dip tube in the flask was connected through a peristaltic pump to a column
  2. additioncontaining 6.0 g of Novozyme 435 which
  3. additioncontaining 6.0 g of dried Amberlyst A-21
  4. customA tube from this second column returned to the original flask
  5. customby removing the column
  6. washwashing the contents with 100 mL of 10% triethylamine in toluene (with 100 mL of toluene chaser)
  7. customApproximately 50% of the contents of the pot (80 mL) was removed
  8. additiona mixture of 11.0 g of 80% retinyl acetate and 7.5 g of linoleic acid in 80 mL of toluene
  9. additionwas added to the pot
  10. waitAfter 9 h 73.6% conversion had been achieved
  11. customApproximately 50% of the contents of the pot (80 mL) was removed
  12. additiona mixture of 11.0 g of 80% retinyl acetate and 7.5 g of linoleic acid in 80 mL of toluene
  13. additionwas added to the pot
  14. waitAfter 12 h 75.0% conversion had been achieved

출처 및 근거

ORD 기록
ord-66c2f5d8940841a38c9fc967397e06e5
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566795B2

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