Vinyl benzoate → Benzoic Acid

HRID 579859

反応式

HRID 579859 の反応式
[C:1]([O:9]C=C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 1

HCID 13037Vinyl benzoate

生成物 1

HCID 243Benzoic Acid

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

A 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar is charged with THF (5 mL), (PPh3)2PdCl2 (0.05 mmol), L-menthoxyethanol (0.5 mmol), and vinyl benzoate (0.5 mmol). The reactor is sealed, pressurized to 1000 psig with CO, and stirred for 24 hours at 100° C. The product mixture, isolated after removal of gas from the reactor vessel, contains a diastereomeric mixture of L-menthoxyethyl benzoyl-L-lactate and L-menthoxyethyl benzoyl-D-lactate. The diastereomers are separated by preparative gas chromatography using an SE-30 liquid phase column. Each diastereomer is hydrolyzed separately by treatment with 2N HCl (aq) for 2 hours at 100° C. to give pure L- and D-lactic acid, benzoic acid, and L-menthoxyethanol, which is thereafter recycled to a repeat of the foregoing hydrocarboxylation reaction.

後処理

  1. customA 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar
  2. customThe reactor is sealed
  3. customThe product mixture, isolated
  4. customafter removal of gas from the reactor vessel
  5. additiona diastereomeric mixture of L-menthoxyethyl benzoyl-L-lactate and L-menthoxyethyl benzoyl-D-lactate
  6. customThe diastereomers are separated by preparative gas chromatography
  7. waitEach diastereomer is hydrolyzed separately by treatment with 2N HCl (aq) for 2 hours at 100° C.

出典と根拠

ORDレコード
ord-cef81fc65e9647529085aab47396ffb5
出典データセット
uspto-grants-1988_06
特許番号
US04749811

関連ノート

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