Methyl phenylacetate → HCID 12940471, compound

HRID 1576460Notes

Reaction equation

HRID 1576460 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 2 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'-chloro-carbonylpropyl)-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-3f0b82a8155442bf97f30a163c7418d7
Source dataset
uspto-grants-1976_09
Patent number
US03980699

Reaction notes

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