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

HRID 638517

反応式

HRID 638517 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)]

出典と根拠

ORDレコード
ord-ac977286982a4baea505408ff4bbdc31
出典データセット
uspto-grants-1985_12
特許番号
US04562005

関連ノート

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