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Hydrochloric Acid → methyl 4-{(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyloxy}-2-hydroxybenzoate

HRID 264357
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HRID 264357 반응식
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Cl)[CH:20]=[C:21]([CH2:23][CH2:24][CH:25]=[C:26]([CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])[CH3:27])[CH3:22].Cl>C(OCC)(=O)C.CN(C=O)C>[CH3:22]/[C:21](/[CH2:23][CH2:24]/[CH:25]=[C:26](\[CH3:27])/[CH2:28][CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])=[CH:20]\[CH2:19][O:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([OH:1])[CH:11]=1
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참가 물질

7

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HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 40734091-Chloro-3,7,11-trimethyldodeca-2,6,10-triene

생성물 1

HCID 69129879methyl 4-{(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyloxy}-2-hydroxybenzoate수율 71%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

In 10 m of DMF were poured 1.28 g (7.6 mmol) of methyl 2,4-dihydroxybenzoate and 1.05 g (7.6 mmol) of potassium carbonate, and 1.84 g (7.6 mmol) of farnesyl chloride was added thereto dropwise at room temperature. After the addition, the mixture was stirred at 60° C. for 3 hours and then poured into a 12% hydrochloric acid aqueous solution. Ethyl acetate was poured thereinto to conduct extraction. The resulting extract was washed with water and a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The resulting crude product was purified by column chromatography on silica gel to obtain 2.0 g (yield: 71%) of methyl 4-{(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienyloxy}-2-hydroxybenzoate represeted by the following structural formula (hereinafter referred to as compound 37) as a colorless, clear and oily substance. The analytical results are shown below. ##STR58##

후처리

  1. additionwas added
  2. customdropwise at room temperature
  3. additionAfter the addition
  4. extractionextraction
  5. extractionThe resulting extract
  6. washwas washed with water
  7. dry with materiala saturated sodium chloride aqueous solution, dried over sodium sulfate
  8. concentrationconcentrated
  9. customThe resulting crude product was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-723c4196c7054f71a9b53fb021786a36
출처 데이터셋
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05646184

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