Hydrochloric Acid → HCID 69618831, compound

HRID 859810Notes

Reaction equation

HRID 859810 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23]C(=O)C)=[C:16]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32]C(=O)C)[CH:15]=[CH:14][C:11]=1[CH:12]=O)(=O)C.C(O)(=O)[CH2:37][C:38]([OH:40])=[O:39].N1CCCCC1.[OH-].[K+].Cl>O.N1C=CC=CC=1>[OH:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=[C:16]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])[CH:15]=[CH:14][C:11]=1[CH:12]=[CH:37][C:38]([OH:40])=[O:39]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 14797Potassium HydroxideHCID 85981197HCID 85981197, compound

Product 1

HCID 69618831HCID 69618831, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

Into a three-neck flask, 2,3,4-tri(4-acetyloxy-butyloxy)benzaldehyde (40.0 g), malonic acid (10.6 g), piperidine (1 ml) and 100 mL of pyridine were added and stirred at 110° C. for 5 hours. After cooling, water (500 ml) and potassium hydroxide (26.0 g) were added and stirred at 60° C. for 2 hours. After cooling, concentrated hydrochloric acid was added until the reaction solution became acidic, and the resulting reaction solution was extracted with ethyl acetate and washed with water. The extract was concentrated and then purified by column chromatography to obtain the titled compound (30.1 g). Yield: 90%.

Workup

  1. temperatureAfter cooling
  2. stirringstirred at 60° C. for 2 hours
  3. temperatureAfter cooling
  4. customthe resulting reaction solution
  5. extractionwas extracted with ethyl acetate
  6. washwashed with water
  7. concentrationThe extract was concentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-88dbb688a5fe4703814d230d655a3fbc
Source dataset
uspto-grants-2006_12
Patent number
US07153548B2

Reaction notes

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