Hydroxyphenylacetic acid → HCID 58611834, compound

HRID 2375226Notes

Reaction equation

HRID 2375226 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH:17][C:18]1C=CC(CC(O)=O)=C[CH:19]=1.C(Cl)(=O)C>N1C=CC=CC=1>[C:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1)(=[O:17])[CH3:19]

Participants

5

Reactant 3

HCID 127Hydroxyphenylacetic acidHCID 6367Acetyl chlorideHCID 570430821358798-21-6

Product 1

HCID 58611834HCID 58611834, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-(4-hydroxyphenyl)cyclohexanecarboxylic acid (10) (1.264 g crude material, obtained from 1.000 g (6.57 mmol) of 9) in pyridine (5 ml) under argon atmosphere at 0° C. acetyl chloride (0.541 g, 7.61 mmol) slowly (ca. over 10 minutes) was added and the mixture was stirred for 15 minutes at this temperature. The ice bath was removed and the reaction mixture was stirred at ambient temperature for 3 hours, then the content was poured into ice water (30 ml) and the pH of the medium was brought to 1-2 by adding conc.HCl. The mixture was extracted with ethyl acetate (2×40 ml), the organic extract was washed successively with water (30 ml), brine (15 ml), and dried (Na2SO4). The solvent was evaporated, the residue was dissolved in toluene and chromatographed on silica gel (100 g) with petroleum ether-dioxane-acetic acid (8:2:0.1) as eluent affording the title compound (0.406 g, 23.5% based on 9) as a white solid. 1H NMR (CDCl3, HMDSO) δ: 1.06-1.98 (8H, m); 2.28 (3H, s); 2.30-2.63 (2H, m); 7.09 (2H, d, J=8.6 Hz); 7.46 (2H, d, J=8.6 Hz); 10.49 (1H, br s).

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction mixture was stirred at ambient temperature for 3 hours
  3. additionthe content was poured into ice water (30 ml)
  4. additionby adding conc
  5. extractionThe mixture was extracted with ethyl acetate (2×40 ml)
  6. extractionthe organic extract
  7. washwas washed successively with water (30 ml), brine (15 ml)
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was evaporated
  10. dissolutionthe residue was dissolved in toluene
  11. customchromatographed on silica gel (100 g) with petroleum ether-dioxane-acetic acid (8:2:0.1) as eluent

Sources & evidence

ORD record
ord-4b8c667bafb14e74836e7e81608672f3
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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