3-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester → 3-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid

HRID 1665906ノート

反応式

HRID 1665906 の反応式
C[O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH:13]=[O:14])=[CH:8][C:7]=1[CH3:15]>CO.[OH-].[Na+]>[CH:13]([C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([CH:5]=[CH:4][C:3]([OH:16])=[O:2])=[C:7]([CH3:15])[CH:8]=1)=[O:14]

参加物

4

反応物 1

HCID 765393073-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester

生成物 1

HCID 765393083-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid収率 81%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a solution of 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester (2.9 g, 13.3 mmol) in methanol (70 mL), 2 N aq. NaOH (35 mL) is added. The suspension is stirred for 30 min at rt. Methanol is evaporated and the aq. solution is extracted twice with DCM. The aq. layer is acidified with 2 N aq. HCl and extracted twice with EA. The combined EA extracts are dried over MgSO4, filtered and evaporated. The crude product is recrystallized from EA to give 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid (2.2 g) as pale yellow crystals; LC-MS: tR=0.83 min; 1H NMR (D6-DMSO): δ 12.65 (s br, 1H), 9.92 (s, 1H), 7.66 (d, J=16.4 Hz, 1H), 7.61 (s, 2H), 6.12 (d, J=16.4 Hz, 1H), 2.35 (s, 6H).

後処理

  1. customMethanol is evaporated
  2. extractionthe aq. solution is extracted twice with DCM
  3. extractionextracted twice with EA
  4. dry with materialThe combined EA extracts are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is recrystallized from EA

出典と根拠

ORDレコード
ord-316e295907ca4a5ab777034fb2232d10
出典データセット
uspto-grants-2011_10
特許番号
US08039644B2

反応ノート

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