Dichloromethane → 4-(4-Hydroxyphenyl)-7-hydroxy-3-phenyl-1,2-dihydronaphthalene

HRID 1926578Notes

Reaction equation

HRID 1926578 reaction equation
ClCCl.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21]C)=[CH:18][CH:19]=3)[CH2:14][CH2:13][C:12]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][CH:6]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.CCCCCC.CCCCCCC>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=3)[CH2:14][CH2:13][C:12]=2[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 200362p-(6-Methoxy-2-phenyl-3,4-dihydro-1-naphthyl)phenol2×HCID 516892Sodium Bicarbonate

Product 1

HCID 595105224-(4-Hydroxyphenyl)-7-hydroxy-3-phenyl-1,2-dihydronaphthaleneYield 98.1%

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

In a reaction vessel, 2.3 ml of dichloromethane was added to the 4-(4-hydroxyphenyl)-7-methoxy-3-phenyl-1,2-dihydronaphthalene (7, 29.7 mg, 0.090 mM) obtained in the above Step (4), and the reaction system was cooled to 0° C. Next, 0.45 ml of a 1 M heptane solution including five equivalents of boron bromide (BBr3) was added. After 1.5 hr had elapsed, thin layer chromatography (n-hexane:ethyl acetate=3:1) was carried out on part of the reaction product, and after confirming that no spot was detected corresponding to the above 4-(4-hydroxyphenyl)-7-methoxy-3-phenyl-1,2-dihydronaphthalene, an aqueous NaHCO3 solution was added and the reaction was stopped. After extracting the reaction product with dichloromethane and ethyl acetate, the organic layer was washed with water and a saturated saline solution, and the organic layer was dried with anhydrous sodium sulfate. After concentrating the organic layer, thin layer chromatography (n-hexane:ethyl acetate 3:1) was carried out, and 27.9 mg of 4-(4-hydroxyphenyl)-7-hydroxy-3-phenyl-1,2-dihydronaphthalene (8) was obtained. The yield was quantitative.

Workup

  1. customobtained in the above Step (4)
  2. additionwas added
  3. extractionAfter extracting the reaction product with dichloromethane and ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materiala saturated saline solution, and the organic layer was dried with anhydrous sodium sulfate
  6. concentrationAfter concentrating the organic layer, thin layer chromatography (n-hexane:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-673dacb7e5484cf1b776b30a79be052d
Source dataset
uspto-grants-2012_05
Patent number
US08183235B2

Reaction notes

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