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Hydrochloric Acid → 2-Oxo-1,2-diphenylethyl 2-[(3-methoxy-phenyl)methyl]cyclohexanecarboxylate

HRID 377298
Notes
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Reaction equation

HRID 377298 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]2[C:28]([OH:30])=[O:29])[CH:18]=[CH:19][CH:20]=1.[C:31]1([C:37]([CH:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)O)=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.Cl>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]2[C:28]([O:30][CH:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:37](=[O:38])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:29])[CH:18]=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8400BenzoinHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19358413HCID 19358413, compound

Product 1

HCID 542348532-Oxo-1,2-diphenylethyl 2-[(3-methoxy-phenyl)methyl]cyclohexanecarboxylateYield 51.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (501 mg) was added to a stirred solution of 2-[(3-methoxyphenyl)methyl]cyclohexanecarboxylic acid (500 mg), benzoin (427 mg), and 4-dimethylaminopyridine (12.2 mg) in dichloromethane (10 ml) under ice cooling. The resulting mixture was stirred at the same temperature for 2 hours and at room temperature for 1 hour, and then a mixture of ethyl acetate and 1N hydrochloric acid was added thereto. The organic layer was separated, washed successively with 1N hydrochloric acid, sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed over silica gel using n-hexane--toluene as an eluent to afford 2-oxo-1,2-diphenylethyl 2-[(3-methoxyphenyl)-methyl]cyclohexanecarboxylate (455 mg) as a colorless oil.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed successively with 1N hydrochloric acid, sodium bicarbonate aqueous solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-f18a4294a93a4ea1969402535974c92e
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06025375

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes