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

HRID 34843Notes

Reaction equation

HRID 34843 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-06b41dc5427645eba3729a21690e8a7e
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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