Hydrochloric Acid → 3-Phenyloxolan-2-one

HRID 1780212Notes

Reaction equation

HRID 1780212 reaction equation
[C:1]1([C:7]([CH2:18][CH2:19][O:20][C:21](=[O:23])C)(C(OCC)=O)C(OCC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([CH:7]2[CH2:18][CH2:19][O:20][C:21]2=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19050130Diethyl alpha-phenyl-alpha-(2-acetoxyethyl)malonate

Product 1

HCID 232693-Phenyloxolan-2-oneYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Example 2 (837 g, 2.6M) methanol (1.5 l) and 40% aq. NaOH (1 l, 10M) were heated to reflux for 2 hours. The reaction was then cooled to room temperature and acidified with conc. HCl (1l). The reaction was left as room temperature overnight and then extracted with methyl tert.butyl ether (1 l,500 ml). The extracts were washed with aq. Na2CO3, dried and evaporated to give the title compound(376 g, 89%).

Workup

  1. temperatureto reflux for 2 hours
  2. extractionextracted with methyl tert.butyl ether (1 l,500 ml)
  3. washThe extracts were washed with aq. Na2CO3
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-7d238d5a0dac4316a959a22dd1e8cc7f
Source dataset
uspto-grants-1997_05
Patent number
US05629432

Reaction notes

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