Hydrochloric Acid → HCID 11816954, compound

HRID 2292125Notes

Reaction equation

HRID 2292125 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].[C:12]1([Mg]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.Cl>CCOCC>[OH:11][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 682662-TetraloneHCID 178418255HCID 178418255, compound

Product 1

HCID 11816954HCID 11816954, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

2-Tetralone (8.76 g) in dry ether (100 ml) was added dropwise to phenyl magnesium bromide (generated from bromobenzene 19.16 g) in dry ether (300 ml). The mixture was refluxed for 1 hr. The reaction mixture was decomposed by careful addition of water. The resulting emulsion was clarified by addition 2M-hydrochloric acid (250 ml) and ether (500 ml). The ether layer was separated and washed with water (100 ml), dilute sodium hydrogen carbonate solution solution (200 ml) and water (100 ml) and dried (magnesium sulphate and evaporated in vacuo to afford 2-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalene as an oil. (8.8 g), characterised by its nmr spectrum

Workup

  1. temperatureThe mixture was refluxed for 1 hr
  2. customThe ether layer was separated
  3. washwashed with water (100 ml), dilute sodium hydrogen carbonate solution solution (200 ml) and water (100 ml)
  4. dry with materialdried (magnesium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-88c70cf62beb4d83943edb1fd22a50a5
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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