Hydrochloric Acid → 2-Methoxy-3-(pentadecyloxy)propan-1-OL

HRID 638517

반응식

HRID 638517 반응식
[CH3:1][O:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[OH-].[K+].Cl>CS(C)=O.O1CCCC1.O>[CH2:23]([O:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:6][OH:7])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 123941-BromopentadecaneHCID 14797Potassium HydroxideHCID 111709312-Methoxypropane-1,3-diol

생성물 1

HCID 202524792-Methoxy-3-(pentadecyloxy)propan-1-OL수율 42.3%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

In a mixture of 30 ml of dimethyl sulfoxide (DMSO) and 30 ml of tetrahydrofuran (THF) were dissolved 10.9 g of 2-methylglycerol and 10 g of 1-bromopentadecane, and 7.7 g of powdered KOH was added at room temperature. The mixture was stirred vigorously for 30 minutes, refluxed for 3.5 hours, poured into 400 ml of water, neutralized with concentrated hydrochloric acid with ice-cooling, and extracted three times with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The oily residue (10 g) was purified by silica gel column chromatography [silica gel: 110 g; eluent: n-hexane-chloroform (2:3)] to give 4.6 g of the above-identified alcohol compound.

후처리

  1. additionwas added at room temperature
  2. temperaturerefluxed for 3.5 hours
  3. temperaturecooling
  4. extractionextracted three times with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe oily residue (10 g) was purified by silica gel column chromatography [silica gel: 110 g; eluent: n-hexane-chloroform (2:3)]

출처 및 근거

ORD 기록
ord-ac977286982a4baea505408ff4bbdc31
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04562005

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