Acetate → 1-(2-Hydroxy-4-tetradecylphenyl)ethanone

HRID 703338Notes

Reaction equation

HRID 703338 reaction equation
[CH2:1]([C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=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-].[Al+3].[Cl-].[Cl-]>CCOCC>[OH:21][C:17]1[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]=[CH:19][C:18]=1[C:22](=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 175AcetateHCID 6451240Aluminum(III) ChlorideHCID 144404953-Tetradecylphenol

Product 1

HCID 142562101-(2-Hydroxy-4-tetradecylphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 20 g portion of 3-tetradecylphenol, acetate was heated at 110° C. and 8.4 g of aluminum chloride was added in portions over a 3 hour period. The mixture was allowed to cool, then diluted with ether, poured onto ice containing 10 ml of concentrated hydrochloic acid and extracted several times with ether. The ether extracts were combined, washed with water, brine and dried. The crude material was chromatographed on silica gel, eluting with hexane:ethyl acetate (50:1), giving 15.8 g of the desired compound, mp 45°-46° C.

Workup

  1. temperatureto cool
  2. additionpoured onto ice containing 10 ml of concentrated hydrochloic acid
  3. extractionextracted several times with ether
  4. washwashed with water, brine
  5. customdried
  6. customThe crude material was chromatographed on silica gel
  7. washeluting with hexane:ethyl acetate (50:1)

Sources & evidence

ORD record
ord-7a35c7be91ee4a0bbbdcf8ba8e91b474
Source dataset
uspto-grants-1991_01
Patent number
US04981989

Reaction notes

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