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Water → Methyl 2-methoxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate

HRID 1131
Notes
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Reaction equation

HRID 1131 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]([C:14]2[CH:27]=[CH:26][C:25]3[C:16](=[CH:17][C:18]4[C:19]([CH3:31])([CH3:30])[CH2:20][CH2:21][C:22]([CH3:29])([CH3:28])[C:23]=4[CH:24]=3)[CH:15]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].I[CH3:33].O>CN(C=O)C>[CH3:33][O:3][C:4]1[CH:13]=[C:12]([C:14]2[CH:27]=[CH:26][C:25]3[C:16](=[CH:17][C:18]4[C:19]([CH3:31])([CH3:30])[CH2:20][CH2:21][C:22]([CH3:29])([CH3:28])[C:23]=4[CH:24]=3)[CH:15]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19694690Methyl 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate

Product 1

HCID 19694670Methyl 2-methoxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

130 mg (4.2 mmol) of sodium hydride (80% in oil) and 20 ml of DMF were introduced into a three-necked flask, a solution of 1.6 g (4.2 mmol) of methyl 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate in 50 ml of DMF was added dropwise and the mixture was stirred until gaseous emission ceased. 340 μl (5.5 mmol) of iodomethane were then added and the mixture was stirred at room temperature for two hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. 1.6 g (96%) of the expected compound was recovered in the form of a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for two hours
  2. extractionextracted with ethyl ether
  3. customthe organic phase decanted
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. custom1.6 g (96%) of the expected compound was recovered in the form of a colorless oil

Sources & evidence

ORD record
ord-d9af6adb5c534d1a86a82222f63dd4ec
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723499

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes