Hydrochloric Acid → HCID 13298050, compound

HRID 2396132Notes

Reaction equation

HRID 2396132 reaction equation
C([O:4][CH2:5][CH2:6][C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[C:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.O.[OH-].[Na+].Cl>C(O)C>[C:15]1([C:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:6][CH2:5][OH:4])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 13298049HCID 13298049, compound

Product 1

HCID 13298050HCID 13298050, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

34.2 g of 4-acetoxy-l,l,2-triphenyl-1-butene are dissolved in 200 ml of 94%ethanol, after which 20 ml of water and 45 ml of a 20% sodium hydroxide solution are added. The mixture is refluxed for 1 h. The solution is neutralized with 2M hydrochloric acid, after which the ethanol is evaporated. Water is added into the residue. The product is extracted in ethyl acetate, the ethyl acetate solution is dried over sodium sulfate andthe solvent is evaporated. The product is recrystallized from a mixture of water and methanol and then has m.p. 117°-9° C. The yield is23.7 g (79%). 1H-NMR-spectrum (CDCl3): δ 1.34 (1H, s), 2.73 (2H, t), 3.05 (2H, t), 6.90 (5H, s), 7.11 (5H, s), 7.25 (5H, s).

Workup

  1. temperatureThe mixture is refluxed for 1 h
  2. customafter which the ethanol is evaporated
  3. additionWater is added into the residue
  4. extractionThe product is extracted in ethyl acetate
  5. dry with materialthe ethyl acetate solution is dried over sodium sulfate andthe solvent
  6. customis evaporated
  7. customThe product is recrystallized from a mixture of water and methanol

Sources & evidence

ORD record
ord-cf2736f4dfb14b9c844a8dd47ac1f4ca
Source dataset
uspto-grants-1996_02
Patent number
US05491173

Reaction notes

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