Hydrochloric Acid → HCID 11413199, compound

HRID 1377931Notes

Reaction equation

HRID 1377931 reaction equation
CO[C:3](OC)([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)[CH3:4].O.Cl.C([O:24]CC)C>O1CCCC1.[Cl-].[Na+].O>[C:9]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:8]=[CH:7][C:6]([O:5][CH2:3][CH:4]=[O:24])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 131720186HCID 131720186, compound

Product 1

HCID 11413199HCID 11413199, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The acetal from Step 1 (2.10 g) was dissolved in 10 mL of tetrahydrofuran and 1 mL of distilled water was added to the yellow solution, followed by 1 mL of concentrated hydrochloric acid. This mixture was stirred rapidly overnight, then a small amount of saturated aqueous brine solution was added to the reaction mixture, followed by 50 mL of diethyl ether. The organics were extracted into the ether layer and the aqueous layer was washed twice more with diethyl ether. The ether layers were combined, dried over anhydrous magnesium sulfate, and evaporated. The residue was triturated with a 10% solution if isopropyl alcohol in chloroform, leaving a white solid. This solid was again triturated with a small amount of methanol in dichloromethane. The yield of filtrates from the above two triturations was 1.84 g (71% ) of 4-biphenyloxyacetaldehyde.

Workup

  1. extractionThe organics were extracted into the ether layer
  2. washthe aqueous layer was washed twice more with diethyl ether
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was triturated with a 10% solution if isopropyl alcohol in chloroform
  6. customleaving a white solid
  7. customThis solid was again triturated with a small amount of methanol in dichloromethane

Sources & evidence

ORD record
ord-25bcb4cd4f7348e6a81ffb97858b7d54
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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