Hydrochloric Acid → 5',6'-Dihydro-5',5'-dimethyl-8'-(4-methylphenyl)-[2,2'-binaphthalene]6-carboxylic acid

HRID 613345노트

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HRID 613345 반응식
[CH3:1][C:2]1([CH3:34])[CH2:11][CH:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:8]2[CH:7]=[C:6]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:29]([O:31]CC)=[O:30])[CH:25]=4)[CH:20]=3)[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+].Cl>CCO>[CH3:1][C:2]1([CH3:34])[CH2:11][CH:10]=[C:9]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[C:8]2[CH:7]=[C:6]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:29]([OH:31])=[O:30])[CH:25]=4)[CH:20]=3)[CH:5]=[CH:4][C:3]1=2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15870725Ethyl 5',6'-dihydro-5',5'-dimethyl-8'-(4-methylphenyl)-[2,2'-binaphthalene]-6-carboxylate2회

생성물 1

HCID 158707265',6'-Dihydro-5',5'-dimethyl-8'-(4-methylphenyl)-[2,2'-binaphthalene]6-carboxylic acid수율 19.4%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

A solution of ethyl 5',6'-dihydro-5',5'-dimethyl-8'-(4-methylphenyl)-[2,2'-binaphthalene]-6-carboxylate (Compound 64) 0.19 g, 0.43 mmol), EtOH (8 ml) and 1N aqueous NaOH (2 ml) was heated to 60° C. for 3 hours. The solution was cooled to 0° C. and acidified with 1N aqueous HCl. The product was extracted into ethyl acetate, and the organic layers combined, washed with water, brine, dried (MgSO4), filtered and the solvent removed in-vacuo. The residue was recrystalized from THF/ethyl acetate at 0° C. to give 35 mg of pure material. The mother liquor was concentrated under reduced pressure and the residue purified by silica gel chromatography (100% ethyl acetate) to give an additional 125 mg of the title compound (overall yield=160 mg, 90%) as a colorless solid. 1H NMR (DMSO-d6) δ 8.57 (s, 1H), 8.11 (d, 1H, J=8.7 Hz), 7.96-7.82 (overlapping d's, 3H),7.65 (d, 2H, J=7.6 Hz), 7.50 (d, 1H, J=7.9 Hz), 7.28 (s, 1H), 7.26 (d, 2H, J=8.3 Hz), 7.21 (d, 2H, J=8.3 Hz), 6.01 (t, 1H, J=4.5 Hz), 3.34 (br s, 1H), 2.31 (s, 3H), 2.31 (d, 2H, J=4.5 Hz), 1.31 (s, 6H).

후처리

  1. extractionThe product was extracted into ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in-vacuo
  6. customThe residue was recrystalized from THF/ethyl acetate at 0° C.

출처 및 근거

ORD 기록
ord-584576b213d44f528bdfa3377c659b08
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008204

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