Hydrochloric Acid → (S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid

HRID 19395ノート

反応式

HRID 19395 の反応式
[OH:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.C(OCC)(=O)C.O>[CH2:14]([O:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C@H:2]([OH:1])[C:3]([OH:5])=[O:4])=[CH:12][CH:11]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 9920545Latifolicinin C acid

生成物 1

HCID 11818113(S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid収率 67%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionic acid (3.00 g, 16.47 mmol) in ethanol (50 mL) was treated with benzyl chloride (4.20 g, 33.18 mmol) and potassium carbonate (4.60 g, 33.28 mmol) and the resulting mixture heated at reflux overnight. The mixture was cooled and treated with water (50 mL), and the resulting mixture stirred for 1 h. At this time ethyl acetate was added and the mixture acidified with 1N aqueous hydrochloric acid. The layers were separated and the aqueous phase extracted with ethyl acetate (3×). The organic phases were combined and concentrated in vacuo to an approximate volume of 10 mL. The resulting mixture was filtered and the isolated solid washed with diethyl ether and dried to afford (S)-3-(4-benzyloxy-phenyl)-2-hydroxy-propionic acid (3.00 g, 67%) as a white solid.

後処理

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux overnight
  3. temperatureThe mixture was cooled
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with ethyl acetate (3×)
  6. concentrationconcentrated in vacuo to an approximate volume of 10 mL
  7. filtrationThe resulting mixture was filtered
  8. washthe isolated solid washed with diethyl ether
  9. customdried

出典と根拠

ORDレコード
ord-7bf4264f92114a73b81e0ad85409f4ab
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

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