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

HRID 329993Notes

Reaction equation

HRID 329993 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-fd38df1517e545fb9918e7196593f463
Source dataset
uspto-grants-1990_01
Patent number
US04894367

Reaction notes

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