Hydrochloric Acid → 3-(1-Adamantyl)-4-methoxybenzoic acid

HRID 710363ノート

反応式

HRID 710363 の反応式
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([C:12]23[CH2:21][CH:16]4[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]4)[CH2:13]2)[CH2:19]3)[CH:5]=1.[OH-].[Na+].CCO.Cl>C1COCC1.O.CCOC(C)=O>[C:12]12([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=3[O:10][CH3:11])[C:3]([OH:22])=[O:2])[CH2:13][CH:14]3[CH2:20][CH:18]([CH2:17][CH:16]([CH2:15]3)[CH2:21]1)[CH2:19]2

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 14549070Methyl 3-(1-adamantyl)-4-methoxybenzoate

生成物 1

HCID 52965033-(1-Adamantyl)-4-methoxybenzoic acid収率 90.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of methyl-3-(1-adamantyl)-4-methoxybenzoate (0.27 g, 0.85 mmol) in THF (30 ml) was added a solution of NaOH (0.04 g) in H2O (1 ml), followed by the addition of EtOH (2 ml). The mixture was refluxed for 4 h, then cooled to room temperature and acidified with 1M HCl solution. The crude product was taken in EtOAc (100 ml) and the organic layer was washed with H2O, and dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title product (0.22 g, 85%) as colourless solid. 1H-NMR (CDCl3) 1.77 (s, 6H), 2.03 (s, 3H), 2.09 (s, 6H), 3.89 (s, 3H), 6.88 (d, 1H, J=8.44 Hz), 7.93-7.98 (m, 2H).

後処理

  1. temperatureThe mixture was refluxed for 4 h
  2. washthe organic layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-fac5522abc9d48c5ac8fac7b3344b96f
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

反応ノート

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