Methyl phenylacetate → HCID 12940471, compound

HRID 1284381Notes

Reaction equation

HRID 1284381 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH2:18][CH2:17]1>C(=S)=S>[C:19]([CH2:18][CH2:17][C:16]([C:4]1[CH:5]=[CH:6][C:1]([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:2][CH:3]=1)=[O:22])([OH:21])=[O:20]

Participants

5

Reactant 3

HCID 7559Methyl phenylacetateHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12940471HCID 12940471, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a mixture of 18 g. of methyl phenylacetate, 26 g. of aluminum chloride and 150 ml. of carbon disulfide, 20 g. of succinic anhydride are added. The reaction mixture is allowed to stand for two hours at 35°C; then it is added to a liter of ice water and extracted with methylene chloride. The extracts are combined, washed, dried, and evaporated to give methyl p-(3'-carboxy-1'-oxopropyl)-phenylacetate. This derivative is reduced with sodium borohydride and dehydroxylated with palladium charcoal catalyst by the procedures described in Part A of Example 2 to afford methyl p-(3'-carboxypropyl)-phenylacetate. This derivative is refluxed in 50 ml. of thionyl chloride for three hours and then it is evaporated. The residue, containing methyl p-(3'-chlorocarbonylpropyl)-phenylacetate, is taken up in 175 ml. of benzene containing 40 g. of aluminum chloride. The resulting mixture is stirred for 2 hours at 20°C; then it is added to a liter of ice and water and extracted with methylene chloride. The extracts are combined, washed with water to neutrality, dried over sodium sulfate, and evaporated to give 7-(methoxycarbonylmethyl)-1-tetralone.

Workup

  1. additionTo a mixture of 18 g
  2. extractionextracted with methylene chloride
  3. washwashed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-dca8247c5fab42f5a23fcd19a44f47bf
Source dataset
uspto-grants-1976_08
Patent number
US03978124

Reaction notes

Loading…