Hydrochloric Acid → HCID 12016860, compound

HRID 1528042Notes

Reaction equation

HRID 1528042 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5]1([CH:13]=[CH:12][CH:11]=[C:9]([OH:10])[C:7]=1O)[OH:6].[CH2:14]([O:21][CH2:22][C:23](Cl)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.CC[O:29]CC>ClCCl>[CH2:14]([O:21][CH2:22][C:23]([C:13]1[C:12]([OH:29])=[CH:11][C:9]([OH:10])=[CH:7][C:5]=1[OH:6])=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1057PyrogallolHCID 3283Diethyl EtherHCID 177085Benzyloxyacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12016860HCID 12016860, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

Anhydrous aluminum trichloride (27.5 g, 206 mmol) was dissolved into 200 mL dichloromethane and cooled to −10° C. A solution of pyrogallol (20 g, 159 mmol) in ether was slowly added dropwise to the reaction mixture. After stirring 10 min at −10° C., a solution of benzyloxy acetyl chloride (26.4 g, 143 mmol) in dichloromethane (30 ml) was added dropwise. The reaction mixture was heated to 50° C. for 24 hours, and then cooled to room temperature. 1N HCl solution was carefully added to the mixture. The organic phase was separated and extracted with dichloromethane twice. The combined organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. Yellow oil product was obtained after filtering and concentration, and further purified by silica gel column chromatography (eluent:methanol/dichloromethane, 1:200) to give the desired white compound (14 g, yield 32.2%).

Workup

  1. temperatureThe reaction mixture was heated to 50° C. for 24 hours
  2. temperaturecooled to room temperature
  3. customThe organic phase was separated
  4. extractionextracted with dichloromethane twice
  5. washThe combined organic phase was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customYellow oil product was obtained
  8. filtrationafter filtering
  9. concentrationconcentration
  10. customfurther purified by silica gel column chromatography (eluent:methanol/dichloromethane, 1:200)

Sources & evidence

ORD record
ord-501102a06f244eb6881de53732b08372
Source dataset
uspto-grants-2015_07
Patent number
US09090583B2

Reaction notes

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