Phenol → HCID 20308543, compound

HRID 1763899Notes

Reaction equation

HRID 1763899 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][N:10]([CH3:14])[CH2:11]2)=[CH:6][CH:5]=1.[CH2:21]([CH:23]1[O:25][CH2:24]1)Br.C1(O)C=CC=CC=1>O1CCCC1.O>[O:25]1[CH2:24][CH:23]1[CH2:21][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:9][N:10]([CH3:14])[CH2:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 20308544HCID 20308544, compound

Product 1

HCID 20308543HCID 20308543, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (0.72g) was added to a solution of 7-hydroxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline (2.33g) in dry tetrahydrofuran (75 ml). Epibromohydrin (4.11 g) was added and the solution refluxed for 2 hr. until thin layer chromatography (alumina, chloroform-ether 1:5) showed the absence of starting phenol. Water (25ml) was added and the mixture extracted with ether. The combined ether layers were dried (MgSO4) and the solvent removed under reduced pressure. The oil was taken up in xylene (50 ml) and evaporated to dryness to give the title compound in quantitative yield. τ (CDCl3) 7.68 (3H,s), 7.55-7.0 (3H,m), 6.95-6.6 (2H,m), 6.4 (2H,s), 6.2-5.65 (3H,m), 3.5-3.1 (3H,m), 2.85 (5H,s).

Workup

  1. temperaturethe solution refluxed for 2 hr
  2. extractionthe mixture extracted with ether
  3. dry with materialThe combined ether layers were dried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-d63466b6881a4d618dc22696a93b7f7e
Source dataset
uspto-grants-1978_09
Patent number
US04113869

Reaction notes

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