Water → HCID 13371463, compound

HRID 2413269Notes

Reaction equation

HRID 2413269 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:28]=2[C:29](O)=[O:30])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>O1CCCC1>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:28]=2[CH2:29][OH:30])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 133714622-[4-(Benzyloxy)anilino]-5-methoxybenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 13371463HCID 13371463, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 10 g of lithium aluminum hydride in 1 in liter dry ether under nitrogen was added over a period of one hour a solution of 35 g of 2-(4-benzyloxyphenylamino)-5-methoxybenzoic acid in 300 ml of tetrahydrofuran. The mixture was heated at reflux for three hours, then cooled, and water (20 ml) was slowly added. The solid material was removed by filtration and the filtrate concentrated in vacuo. The residue was crystallized and recrystallized from a benzene-cyclohexane-hexane mixture to yield 26 g of 2-(4-benzyloxyphenylamino)-5-methoxybenzenemethanol, light tan crystals, m.p. 100°-101° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for three hours
  3. temperaturecooled
  4. customThe solid material was removed by filtration
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was crystallized
  7. customrecrystallized from a benzene-cyclohexane-hexane mixture

Sources & evidence

ORD record
ord-c3688431fe434e6d86337413e2f29d94
Source dataset
uspto-grants-1985_01
Patent number
US04496590

Reaction notes

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