Sodium Hydroxide → HCID 10763649, compound

HRID 1078502Notes

Reaction equation

HRID 1078502 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13](/[C:19](/[CH3:31])=[CH:20]\[C:21]4[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+]>CO>[C:1]12([C:11]3[CH:12]=[C:13](/[C:19](/[CH3:31])=[CH:20]/[C:21]4[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19429696HCID 19429696, compound

Product 1

HCID 10763649HCID 10763649, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 g (7.2 mol) of methyl 4-[(Z)-2-(3-(1-adamantyl)-4-methoxyphenyl)propenyl]benzoate are treated with 4 g of sodium hydroxide in 50 ml of methanol and refluxed for 2 h 30min. After evaporation, the reaction medium is treated under the conditions described in Example 1(b). After recrystallization from absolute ethanol, 2.4 g (84%) of 4-[(Z)-2-(3-(1-adamantyl)-4-methoxyphenyl)propenyl]benzoic acid are isolated, which acid melts at 267° C.

Workup

  1. temperaturerefluxed for 2 h 30min
  2. customAfter evaporation
  3. additionthe reaction medium is treated under the conditions
  4. customAfter recrystallization from absolute ethanol, 2.4 g (84%) of 4-[(Z)-2-(3-(1-adamantyl)-4-methoxyphenyl)propenyl]benzoic acid
  5. customare isolated

Sources & evidence

ORD record
ord-4599bd65522f4615a8490cbb9b6a10f0
Source dataset
uspto-grants-1996_08
Patent number
US05547983

Reaction notes

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