Sodium Hydroxide → Z-4-[4-(2-benzyloxyethoxy)-phenyl]-3,4-diphenyl-but-3-en-1-ol

HRID 1636934Notes

Reaction equation

HRID 1636934 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH2:5]/[C:6](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:7](/[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:27]([O:34][CH2:35][CH2:36]Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:27]([O:34][CH2:35][CH2:36][O:20][C:17]1[CH:16]=[CH:15][C:14](/[C:7](/[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6](\[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)/[CH2:5][CH2:4][OH:3])=[CH:19][CH:18]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 13298065Z-4-(4-hydroxy-1,2-diphenyl-but-1-enyl)-phenol

Product 1

HCID 70117020Z-4-[4-(2-benzyloxyethoxy)-phenyl]-3,4-diphenyl-but-3-en-1-ol

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

The reaction vessel was charged with toluene (790 ml), 48% aqueous sodium hydroxide (790 ml), tetrabutylammonium bromide (2.12 g, 6.6 mmol) and Z-4-(4-hydroxy-1,2-diphenyl-but-1-enyl)-phenol (50 g, 0.16 mol) prepared by the method described by U.S. Pat. No. 4,996,225. The mixture was refluxed for 30 minutes. Benzyl-(2-bromoethyl)ether (Grobelny D. et al., Tetrahedron Letters 28, 2639-42, 1979) (41.7 g, 0.19 mol) was added to the reaction mixture and the refluxing was continued for 2 hours. Then the mixture was cooled to room temperature, layers were separated and aqueous phase was washed with toluene. Toluene phases were combined, washed with water, dried and evaporated to dryness. The residue was used in the next stage without further purification.

Workup

  1. customprepared by the method
  2. temperatureThe mixture was refluxed for 30 minutes
  3. customlayers were separated
  4. washaqueous phase was washed with toluene
  5. washwashed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue was used in the next stage without further purification

Sources & evidence

ORD record
ord-057d226e0d114ca1a28ba5e114189eb7
Source dataset
uspto-grants-2000_03
Patent number
US06037379

Reaction notes

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