Ethanol → HCID 13000823, compound

HRID 1533504Notes

Reaction equation

HRID 1533504 reaction equation
[CH2:1](Cl)Cl.CO[C:6]1[CH:7]=[CH:8][C:9]([CH:12]=O)=[CH:10][CH:11]=1.[OH-:14].[Na+].[CH2:16]([OH:18])[CH3:17]>>[C:9]1([C@H:12]2[CH2:17][CH2:16][O:18][C:1]2=[O:14])[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 13000823HCID 13000823, compound

Procedure

Progress of the reaction is monitored by thin layer chromatography (Silica gel plates, eluent methylene chloride; visualization by dipping in a solution of 5% anisaldehyde in ethanol and heating). When the reaction is complete as judged by thin layer chromatography, the reaction mixture is adjusted to a pH of 13 with 10 M sodium hydroxide and then extracted 3 times with 250 ml of methylene chloride. The pH of the aqueous mixture is then adjusted to 3 with concentrated HCl, followed by continuous extraction with 1 liter of ethyl acetate for 24 hours. The ethyl acetate extract is dried over anhydrous magnesium sulfate and evaporated under reduced pressure to yield (R)-2-phenylbutyrolactone as a yellowish solid.

Workup

  1. temperatureheating)
  2. extractionextracted 3 times with 250 ml of methylene chloride
  3. extractionfollowed by continuous extraction with 1 liter of ethyl acetate for 24 hours
  4. extractionThe ethyl acetate extract
  5. dry with materialis dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1a3bf6a9740d4f098b693681378c179d
Source dataset
uspto-grants-2001_03
Patent number
US06207862B1

Reaction notes

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