Hydrochloric Acid → 1-(2-Hydroxy-5-tetradecylphenyl)-1-hexanone

HRID 703328Notes

Reaction equation

HRID 703328 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:11][CH:10]=1)(=O)CCCCC.[Cl-].[Al+3].[Cl-].[Cl-].Cl>CCOCC>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:13][C:14]=1[C:9](=[O:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 14819667Hexanoic acid, 4-tetradecylphenyl ester

Product 1

HCID 142562081-(2-Hydroxy-5-tetradecylphenyl)-1-hexanoneYield 170.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a melted liquid of 38.8 g of hexanoic acid, 4-tetradecylphenyl ester at 80°-95° C. was added 26.67 g of aluminum chloride in small portions over a period of 2 hours. This mixture was heated for an additional hour, then allowed to cool, diluted with ether and poured onto ice containing 10 ml of concentrated hydrochloric acid. The organic layer was washed with water, dried and the solvent evaporated. The residue was chromatographed on silica gel, eluting with hexane:ethyl acetate (50:1), giving 33 g of the desired compound, mp 41°-42° C.

Workup

  1. temperatureThis mixture was heated for an additional hour
  2. temperatureto cool
  3. washThe organic layer was washed with water
  4. customdried
  5. customthe solvent evaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with hexane:ethyl acetate (50:1)

Sources & evidence

ORD record
ord-e659771a6c0d41f598e6a7b8fcebc78b
Source dataset
uspto-grants-1991_01
Patent number
US04981989

Reaction notes

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