Hydrochloric Acid → HCID 11682457, compound

HRID 2390602Notes

Reaction equation

HRID 2390602 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C[O:19][C:20](=[O:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br.Cl>O.CS(C)=O>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]([OH:32])=[O:19])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 804592-BenzyloxyphenolHCID 223913Methyl 11-bromoundecanoate

Product 1

HCID 11682457HCID 11682457, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a 250 mL Erlenmeyer flask was added freshly ground potassium hydroxide (4.2 g, 74.91 mmol) and 100 mL dimethyl sulfoxide. 2-benzyloxy-phenol (5 g, 24.97 mmol) and 11-bromoundecanoic acid methyl ester (7 g, 25.07 mmol) was added and the mixture was allowed to stir at room temperature overnight. Water (75 mL) was added and the solution was heated to 85° C., with stirring, for 3 hours. The reaction was cooled to room temperature and acidified with concentrated hydrochloric acid to pH 2. The acidified solution was cooled to 4° C. for 2 hours, and the precipitate then collect by suction filtration. The product was recrystallized form ethanol/water. The product (8.88 g, 93%) was isolated as a light brown solid, mp 62-63° C. Combustion analysis: Found: C, 74.71; H, 8.08%; C24H32O4 requires C, 74.97; H, 8.39%;

Workup

  1. temperaturethe solution was heated to 85° C.
  2. stirringwith stirring, for 3 hours
  3. temperatureThe reaction was cooled to room temperature
  4. temperatureThe acidified solution was cooled to 4° C. for 2 hours
  5. filtrationthe precipitate then collect by suction filtration
  6. customThe product was recrystallized form ethanol/water

Sources & evidence

ORD record
ord-342460b807c04802b173a6985c603fc9
Source dataset
uspto-grants-2012_09
Patent number
US08273794B2

Reaction notes

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