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

HRID 710363노트

반응식

HRID 710363 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 52965033-(1-Adamantyl)-4-methoxybenzoic acid수율 90.4%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fac5522abc9d48c5ac8fac7b3344b96f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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