Hydrochloric Acid → 1-(2-Hydroxy-4-tetradecylphenyl)-1-hexanone

HRID 34849Notes

Reaction equation

HRID 34849 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([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:10]=1)(=O)CCCCC.[Cl-].[Al+3].[Cl-].[Cl-].Cl>CCOCC>[OH:8][C:9]1[CH:10]=[C:11]([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:12]=[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 14819672HCID 14819672, compound

Product 1

HCID 148196731-(2-Hydroxy-4-tetradecylphenyl)-1-hexanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 14.28 g portion of hexanoic acid, 3-tetradecylphenyl ester was heated to 90°-100° C., then 9.81 g of aluminum chloride was added in portions over 2 hours. Heating was continued for an additional hour, then the mixture was allowed to cool, diluted with ether and poured onto a mixture of ice and concentrated hydrochloric acid. The ether layer was washed with water, then dried and the solvent removed, giving 7 g of the desired compound, mp 44°-45° C.

Workup

  1. temperatureHeating
  2. waitwas continued for an additional hour
  3. temperatureto cool
  4. washThe ether layer was washed with water
  5. customdried
  6. customthe solvent removed

Sources & evidence

ORD record
ord-6ec77afcbe7d48d18df00858fe0e0fb6
Source dataset
uspto-grants-1988_08
Patent number
US04762942

Reaction notes

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