Sodium hydride → Methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyloxy)benzoate

HRID 1275610

Reaction equation

HRID 1275610 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([OH:14])[CH:5]=[CH:4][C:3]1=2.[H-].[Na+].I[C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1>[Cu](Br)Br.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([O:14][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 69273Methyl 4-iodobenzoateHCID 2687865,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 10337221Methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 1049PyridineSolvent

Procedure

5.3 g (15 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthol and 70 ml of pyridine were introduced into a three-necked flask under a nitrogen stream, and 430 mg (15 mmol) of sodium hydride (80% in oil) were added in small amounts. The mixture was stirred for 30 minutes, 3.9 g (15 mmol) of methyl 4-iodobenzoate and 4.6 g (22.5 mmol) of a copper bromide and dimethyl sulfide complex were added successively and the resulting mixture was heated at reflux for 16 hours. The reaction medium was evaporated to dryness, taken up in water and ethyl ether, the organic phase decanted off, dried over magnesium sulfate and evaporated.

Workup

  1. additionwere added in small amounts
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 16 hours
  4. customThe reaction medium was evaporated to dryness
  5. customethyl ether, the organic phase decanted off
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-2f3fa2a9de9e4c4081e8da7291a541f3
Source dataset
uspto-grants-2000_12
Patent number
US06162815

Linked notes

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