Water → Phenyl 3-(1-adamantyl)-4-methoxybenzoate

HRID 129675Notes

Reaction equation

HRID 129675 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:10]12([C:20]3[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=3[O:29][CH3:30])[C:23](Cl)=[O:24])[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2.O>C1COCC1>[C:10]12([C:20]3[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=3[O:29][CH3:30])[C:23]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:24])[CH2:11][CH:12]3[CH2:18][CH:16]([CH2:15][CH:14]([CH2:13]3)[CH2:19]1)[CH2:17]2

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 108044973-(1-Adamantyl)-4-methoxybenzoyl chloride

Product 1

HCID 14852512Phenyl 3-(1-adamantyl)-4-methoxybenzoateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a manner analogous to Example 3(b), 0.95 g (10 mmoles) of phenol in 10 ml of THF are treated with 332 mg (11 moles) of sodium hydride (80% in oil). There is then slowly introduced a solution of 3.2 g (10 mmoles) of 3-(1-adamantyl)-4-methoxybenzoyl chloride in 30 ml of THF. The reaction is permitted to proceed at ambient temperature for 4 hours. The reaction medium is poured into water, extracted with ethyl ether, washed with water, dried on magnesium sulfate and evaporated. The residue is chromatographed on silica, eluting with a 60:40 mixture of hexane and dichloromethane. After evaporation and precipitation in hexane, 3 g (83% yield) of the expected ester having a melting point of 165°-166° C. are isolated.

Workup

  1. extractionextracted with ethyl ether
  2. washwashed with water
  3. customdried on magnesium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on silica
  6. washeluting with a 60:40 mixture of hexane and dichloromethane
  7. customAfter evaporation and precipitation in hexane

Sources & evidence

ORD record
ord-0a4918a368174b3faf9f655c0036ce6a
Source dataset
uspto-grants-1995_11
Patent number
US05468897

Reaction notes

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