HCID 15378089, compound → HCID 15378090, compound

HRID 1612034Notes

Reaction equation

HRID 1612034 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13](/[CH:24]=[CH:25]/[C:26]4[CH:36]=[CH:35][C:29]([C:30]([O:32]CC)=[O:31])=[CH:28][CH:27]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>[OH-].[Na+]>[C:1]12([C:11]3[CH:12]=[C:13](/[CH:24]=[CH:25]/[C:26]4[CH:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[CH:35][CH:36]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

3

Reactant 1

HCID 15378089HCID 15378089, compound

Product 1

HCID 15378090HCID 15378090, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2.0 g (4.0 mmol) of ethyl 4-[(E)-2-[3-(1-adamantyl)-4-methoxyethoxymethoxyphenyl)ethenyl]-benzoate and methanolic sodium hydroxide solution (1.6 g of sodium hydroxide in 50 ml of methanol) were introduced into a round-bottomed flask. The mixture was refluxed for four hours and evaporated to dryness, and the residue was taken up in water and acidified to pH 1. The aqueous phase was extracted with ethyl acetate and the organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was triturated from the minimum amount of ethyl ether, filtered and dried. 1.4 g (74%) of the expected acid, with a melting point of 207–208° C., was collected.

Workup

  1. temperatureThe mixture was refluxed for four hours
  2. customevaporated to dryness
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. customthe organic phase was separated out
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue obtained
  8. customwas triturated from the minimum amount of ethyl ether
  9. filtrationfiltered
  10. customdried
  11. custom1.4 g (74%) of the expected acid, with a melting point of 207–208° C., was collected

Sources & evidence

ORD record
ord-e1f87992557446c0a5f944d00e02b60d
Source dataset
uspto-grants-2006_01
Patent number
US06992095B2

Reaction notes

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