Experiment Number 1: Synthesis of p-Hydroxyacetophenone from Phenol and Acetyl chloride.

Apparatus: 1. Two neck round bottom Flask

2. Quick fit thermometer

3. Stir machine

4. Steel Bowl

Theory:
We will synthesize p-Hydroxyacetophenone from Acetylation of phenol in the presence of catalyst FeCl3 and solvent dichloromethane.

Chemicals used in Experiment:

Phenol:
C6H6O C6H6O Phenol Carbolic acid

Formula Compound Formula Name IUPAC Name Structural Diagram:

Basic properties: 94.1112g/mol Solid(at stp) 40-42C (lit.) 181-182 C(lit.) 1.071g/Cm3 0.09 psi (55C) 0.36 mmHg(20C) 1.5425

Molecular weight Phase Melting point Boiling point Density Vapor pressure Refractive index Chemical identification:

CAS number

108-95-2

Acetyl chloride:
CH3COCl C2H3ClO Acetyl chloride

Formula Compound Formula Name

Structural Diagram:

Basic properties: Molecular weight Phase Melting point Boiling point Density Solubility Dynamic Viscosity Vapor pressure Surface tension Refractive index Chemical Identification: CAS Number 75-36-5 78.498g/mol Liquid -112C 52C (lit.) 1.104 g/Cm3 at 25 C (lit.) Insoluble in Water 3.65*10^-4 pa s (at 25C) 604.4 mmHg 11.69 psi (20C) 32.33 psi (55C) 0.0267. N/m n 20/D 1.389 (lit.)

Dichloromethane:
CH2Cl2 Methylene chloride Dichloromethane

Formula Name IUPAC Name Structural Diagram:

Basic properties: Molecular weight Phase Melting point Boiling point Density Surface tension Dynamic Viscosity Vapor pressure 84.93G/mol Liquid 97 C(lit.) 39.8-40 C mmHg(lit.) 1.325 g/mL at 25 C(lit.) 0.02736 N/m 4.13*10^-4 pa s (at 25C) 24.45 psi ( 55 C)

Refractive index Chemical Identification: CAS Number

6.83 psi ( 20 C) n20/D 1.424(lit.)

75-09-2

Ferric chloride:
FeCl3 Cl3Fe Iron(III) chloride Trichloroiron

Formula Compound Formula Name IUPAC Name Basic properties: Molecular weight Phase Melting point Vapor pressure Chemical Identification: CAS Number

162.2 g/mol (anhydrous) Solid 304C 0.9998 mmHg

7705-08-0

Procedure:
Add 10 mL methylene dichloride and gradually add 18 g of FeCl3 Under stirring at room temp. Reaction mass was chilled to 10C. Mixture of phenol and MDC(i.e 15g phenol+8g MDC was added to reaction mass maintaining temp bellow 15C. Stirred For 30 mins. Chilled to -5 to 0c and add Acetyl chloride. Maintained reaction mass for two hours at -5 to 0C. Reaction completion was monitored by TLC.

TLC:
Material;
1. (TLC) plates (5 x10 cm Silica gel 60)
2. glass capillaries with 1 or 5 micro L volume 3. TLC tanks.

Mobile phase:
1. Eathyl acetate:Hexane (30:70)

Staionary phase:
1. TLC) plates (5 x10 cm Silica gel 60)

Sample preparation:
1 mL of reaction mass was quenched in ice water +HCl mixture, white solid which precipitated out was dissolved in methanol .

Procedure:
1. Mark pencil line 1 cm above from bottom. 2. Spot sample. 3. Place a TLC plate in solvent tank. Make sure the solvent does not touch product sample. 4. After development remove TLC plate. 5. Dry it. 6. Check spots in UV-VIS light. If TLC doesnt comlify reaction mass maintained for 10mins more. If TLC Complify then reaction mass was quenched in mixture of ice water+HCl mixture bellow 25C. Stir for 30 mins. Filtered Dried to obtain white solid of p-Hydroxyacetophenone. Scheme: