Water → HCID 66818585, compound

HRID 12990Notes

Reaction equation

HRID 12990 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=[CH:21]5)[CH:14]=[CH:15][C:16]=3[OH:17])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH3:34]I.O>CN(C=O)C>[C:1]12([C:11]3[CH:12]=[C:13]([C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=[CH:21]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:34])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86625832HCID 86625832, compound

Product 1

HCID 66818585HCID 66818585, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 6-(3-adamantyl-4-hydroxyphenyl)naphtoate (506 mg, 1.23 mmol) was added to an ice-cooled suspension of NaH (80 mg, 60%) in dry DMF, the mixture stirred 1 h at 0° C., then added with 245 mg (1.7 mmol) of CH3I, and left 90 min at r.t. Taking up with 80 ml of cold water, repeated extraction with CH2Cl2, then with EtOAc, drying and evaporating the joined organic phases, and chromatography (silicagel, hexane/EtOAc 9/1) gave 300 mg of methyl 6-(3-adamantyl-4-methoxyphenyl)naphtoate. This compound (235 mg) was suspended in a 1M solution of NaOH in MeOH and the mixture was refluxed 8 h. Evaporation, taking up with water, addition of HCl and filtration gave 227 mg of 6-(3-adamantyl-4-methoxyphenyl)naphtoic acid, mp >300° C.

Workup

  1. temperaturecooled
  2. waitleft 90 min at r.t
  3. extractionextraction with CH2Cl2
  4. dry with materialwith EtOAc, drying
  5. customevaporating the joined organic phases, and chromatography (silicagel, hexane/EtOAc 9/1)

Sources & evidence

ORD record
ord-0ef60b010eb14d4f9a5a713dbe51c995
Source dataset
uspto-grants-2010_06
Patent number
US07728039B2

Reaction notes

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