Water → Methyl 4-[3-(1-adamantyl)-4-methoxybenzoyloxy]-2-hydroxybenzoate

HRID 1729531Notes

Reaction equation

HRID 1729531 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[C:20]12([C:30]3[CH:31]=[C:32]([CH:36]=[CH:37][C:38]=3[O:39][CH3:40])[C:33](Cl)=[O:34])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2.O>C1COCC1>[C:20]12([C:30]3[CH:31]=[C:32]([CH:36]=[CH:37][C:38]=3[O:39][CH3:40])[C:33]([O:12][C:10]3[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([OH:1])[CH:11]=3)=[O:34])[CH2:21][CH:22]3[CH2:28][CH:26]([CH2:25][CH:24]([CH2:23]3)[CH2:29]1)[CH2:27]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 16523Methyl 2,4-DihydroxybenzoateHCID 108044973-(1-Adamantyl)-4-methoxybenzoyl chloride

Product 1

HCID 14852500Methyl 4-[3-(1-adamantyl)-4-methoxybenzoyloxy]-2-hydroxybenzoateYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a round bottom flask, there are introduced 1.68 g (10 mmoles) of methyl 2,4-dihydroxybenzoate, 1.55 ml (11 moles) of triethylamine and 50 ml of THF. There is then slowly added a solution of 3 g (10 mmoles) of 3-(1-adamantyl)-4-methoxybenzoyl chloride in 50 ml of THF and the mixture is stirred at ambient temperature for 12 hours. The reaction medium is poured into water and extracted with ethyl ether. The organic phase is decanted, washed with water, dried on magnesium sulfate and evaporated. The resulting residue is purified by chromatography on a silica column eluted by a 50:50 mixture of dichloromethane and hexane. After evaporation of the solvents, 2.55 g (59% yield) of methyl 4-[3-(1-adamantyl)-4-methoxybenzoyloxy]-2-hydroxybenzoate having a melting point of 125°-127° C. are recovered.

Workup

  1. extractionextracted with ethyl ether
  2. customThe organic phase is decanted
  3. washwashed with water
  4. customdried on magnesium sulfate
  5. customevaporated
  6. customThe resulting residue is purified by chromatography on a silica column
  7. washeluted by a 50:50 mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-b34eefa4209f4e1fa977e8ddbb305f9f
Source dataset
uspto-grants-1994_07
Patent number
US05332856

Reaction notes

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