2-Phenylethanol → 2-Chloro-1-[4-(2-hydroxyethyl)phenyl]ethan-1-one

HRID 1534622Notes

Reaction equation

HRID 1534622 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][C:7](Cl)=[O:8].[CH2:10]([OH:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[Cl:5][CH2:6][C:7]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][OH:18])=[CH:13][CH:14]=1)=[O:8]

Participants

5

Reactant 3

HCID 60542-Phenylethanol2×HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 450809392-Chloro-1-[4-(2-hydroxyethyl)phenyl]ethan-1-oneYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

Finely ground AlCl3 (92.0 g, 0.69 mol) was mixed with dichloromethane (120 ml) in a flask and cooled to -10° C. Chloracetyl chloride (37.3 g, 0.33 mol) was added to the mixture as it was kept cool. Phenethyl alcohol (36.6 g, 0.30 mol) was dissolved in dichloromethane (20 ml) and charged to a dropping funnel. The phenethyl alcohol solution was added slowly dropwise to the mixture over 2 hours while stirring and keeping the temperature at about 10° C. At the end of the addition, the mixture was allowed to warm to room temperature and stirred overnight. The red color solution was poured into a large quantity of ice (about 300 g). The organic layer was separated and the aqueous layer was extracted with dichloromethane (200 ml), and the dichloromethane portions were washed with water until neutral. The organic phase was then dried (magnesium sulfate), concentrated, recrystallized (ether), and dried to give 48.8 g (81.9%) of compound 5. Analysis of the products gave the following results: mp 41°-45° C.; NIR (KBr) 3477, 3355, 2947, 1702, 1693, 1606, 1218, 1044, 818 cm-1 ; 1H NMR (60 MHz) δ 1.96 (s, 1H), 2.92 (t, 2H, J=6.5 Hz), 3.90 (t, 2H, J=6.5 Hz), 4.67 (s,2H), 7.2-7.4 (m, 2H), 7.8-8.0 (m, 2H).

Workup

  1. temperaturewas kept cool
  2. additioncharged to a dropping funnel
  3. customat about 10° C
  4. additionAt the end of the addition
  5. temperatureto warm to room temperature
  6. stirringstirred overnight
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted with dichloromethane (200 ml)
  9. washthe dichloromethane portions were washed with water until neutral
  10. dry with materialThe organic phase was then dried (magnesium sulfate)
  11. concentrationconcentrated
  12. customrecrystallized (ether)
  13. customdried

Sources & evidence

ORD record
ord-3194af1f05f640da9f051a84c947d0ac
Source dataset
uspto-grants-1992_02
Patent number
US05089585

Reaction notes

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