Phosphorus oxychloride → HCID 20337439, compound

HRID 1706251Notes

Reaction equation

HRID 1706251 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]([CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:10].[C:20]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][C:26]1=O)(OCC)=[O:21].P(Cl)(Cl)(Cl)=O>>[OH:1][C:2]1[C:3]([CH:9]([CH3:10])[CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:4][C:5]2[O:8][C:20](=[O:21])[C:25]3[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=3[C:6]=2[CH:7]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 20337452HCID 20337452, compound

Product 1

HCID 20337439HCID 20337439, compound

Procedure

A mixture of 5.0 g. (19.5 mmoles) of 2-(2',5'-dihydroxyphenyl)-5-phenylpentane, 3.4 g. (21.7 mmoles) 2-carboethoxycyclohexanone and 1.78 ml. (19.5 mmoles) of phosphorus oxychloride was stirred for five days under a nitrogen atmosphere. The solidified reaction mixture was dissolved in 175 ml. of chloroform, washed with 3×50 ml. of water and 50 ml. of saturated sodium bicarbonate solution, dried (MgSO4) and evaporated to dryness at reduced pressure to obtain 13.8 g. of a partially crystalline solid. Trituration with hexane and evaporation of the filtrate gave 6.0 g. of crude product, M.P. 184°-193° C. Recrystallization from chloroform-hexane provided 2.66 g. of the title compound as tan crystals; M.P. 201°-203° C. A second crop, 1.7 g. was obtained from the mother liquor. 1H-NMR(CDCl3)ppm, (δ): 7.4-7.1 (m,5,phenyl), 7.1 and 7.05 (s,1,aromatic), 3.6-3.0 (m,1,CH), 2.9-2.3 (m,6,benzylic and allylic CH2), 1.9-1.4 (m,8,CH2), 1.2 (d,3,J=7), α-CH3); IR(KBr) 6.0μ; Mass spectrum (m/e): 362(M+).

Workup

  1. additionA mixture of 5.0 g
  2. customThe solidified reaction mixture
  3. dissolutionwas dissolved in 175 ml
  4. washof chloroform, washed with 3×50 ml
  5. dry with materialof saturated sodium bicarbonate solution, dried (MgSO4)
  6. customevaporated to dryness at reduced pressure
  7. customto obtain 13.8 g
  8. customTrituration with hexane and evaporation of the filtrate
  9. customgave 6.0 g
  10. customRecrystallization from chloroform-hexane
  11. customprovided 2.66 g

Sources & evidence

ORD record
ord-4738d8f1d88241668f50deb1e46af607
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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