Hydrochloric Acid → (2-Hydroxy-4-pentadecylphenyl)(phenyl)methanone

HRID 2309848Notes

Reaction equation

HRID 2309848 reaction equation
C([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:11]=1)(=O)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[OH2:36]>>[OH:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:13]=[CH:14][C:15]=1[C:16]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:10][CH:11]=1)=[O:36]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 20184921HCID 20184921, compound

Product 1

HCID 20184914(2-Hydroxy-4-pentadecylphenyl)(phenyl)methanone

Procedure

3-Pentadecylphenyl benzoate (1.366 g) is finely powered, mixed with pulverised anhydrous aluminium chloride (0.616 g) and the intimate miture is heated to 165° during fifteen minutes. After hydrogen chloride evolution has ceased, the cooled mixture is treated with water, concentrated hydrochloric acid added, and the whole thoroughly stirred to decompose the aluminium complex. The product is ethereally extracted and the dried ethereal layer is concentrated to give the crude product (1.348 g) which possesses a greenish ferric chloride reaction. Chromatographic purification and crystallisation from light petroleum (40°-60°) afford 2-hydroxy-4-pentadecylbenzophenone, m.p. 46°-47°.

Workup

  1. temperaturethe intimate miture is heated to 165° during fifteen minutes
  2. additionadded
  3. extractionThe product is ethereally extracted
  4. concentrationthe dried ethereal layer is concentrated
  5. customto give the crude product (1.348 g) which
  6. customChromatographic purification and crystallisation from light petroleum (40°-60°)

Sources & evidence

ORD record
ord-5ef7882a85354884a13555d04469cddd
Source dataset
uspto-grants-1987_09
Patent number
US04697038

Reaction notes

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