1-Phenylethanol → HCID 20460301, compound

HRID 543667Notes

Reaction equation

HRID 543667 reaction equation
[Br:1][CH:2]1[CH:8]([OH:9])[CH2:7][CH:6]2[CH:3]1[CH2:4][C:5]2=[O:10].[CH3:11][CH:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>[Br:1][CH:2]1[CH:8]([O:9][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:11])[CH2:7][CH:6]2[CH:3]1[CH2:4][C:5]2=[O:10]

Participants

5

Reactant 2

HCID 74091-PhenylethanolHCID 12493710HCID 12493710, compound

Product 1

HCID 20460301HCID 20460301, compoundYield 128.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-bromo-3-hydroxybicyclo[3.2.0]heptan-6-one (15 g), α-methylbenzyl alcohol (36 g) and p-toluene-sulphonic acid (1 g) was heated at 90° for 6 h. The solution was poured into 8% sodium bicarbonate (300 ml) and extracted with ether (4×150 ml). The combined extracts were washed with brine (300 ml), dried (MgSO4) and evaporated to afford crude 2-bromo-3-(1-phenylethoxy)bicyclo[3.2.0]heptan-6-one as a pale yellow oil (29.1 g). The crude product (28.1 g) was dissolved in acetone (50 ml) and treated with morpholine (19 ml). The mixture was stirred for 3 h, poured into water (200 ml) and extracted with ether (4×150 ml). The combined extracts were washed with brine (200 ml), dried (MgSO4) and evaporated. The product was purified by chromatography on silica eluting with ether-petroleum ether (7:3) to give the title compound as a waxy solid (15.7 g). I.R. (CHBr3) 1745 cm-1.

Workup

  1. temperaturewas heated at 90° for 6 h
  2. extractionextracted with ether (4×150 ml)
  3. washThe combined extracts were washed with brine (300 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-fe119132f4334f5e9d81c9b52e8a5980
Source dataset
uspto-grants-1984_05
Patent number
US04447428

Reaction notes

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