Acetate → 1-(2-Hydroxy-5-tetradecylphenyl)ethanone

HRID 34837Notes

Reaction equation

HRID 34837 reaction equation
[CH2:1]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:22]([O-])(=[O:24])[CH3:23].[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)(Cl)Cl>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:20][C:19]=1[C:22](=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 175AcetateHCID 116800TetradecylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 142562051-(2-Hydroxy-5-tetradecylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

A 900 mg portion of 4-tetradecylphenol, acetate was heated at 70° C. under argon and 720 mg of aluminum trichloride was added portionwise. After 2 hours the temperature was raised to 120° C. and the mixture was heated at this temperature for 45 minutes. The mixture was then cooled, diluted with chloroform, washed with 50% aqueous hydrochloric acid then water and dried. The solvents were removed and the residue recrystallized from ether-methanol, giving 850 mg of the desired compound, mp 38.5°-39.5° C.

Workup

  1. temperaturethe mixture was heated at this temperature for 45 minutes
  2. temperatureThe mixture was then cooled
  3. washwashed with 50% aqueous hydrochloric acid
  4. dry with materialwater and dried
  5. customThe solvents were removed
  6. customthe residue recrystallized from ether-methanol

Sources & evidence

ORD record
ord-a0c39a719d2540c3a08a8538995ac0d6
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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