Water → 7-(3-Phthalimidopropoxy)-tetralone

HRID 1905718Notes

Reaction equation

HRID 1905718 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH2:17][CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].O>CN(C)C=O>[C:21]1(=[O:30])[N:20]([CH2:19][CH2:18][CH2:17][O:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][C:9]3=[O:12])=[CH:4][CH:3]=2)[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]12

Participants

6

Reactant 4

HCID 962WaterHCID 21611N-3-BromopropylphthalimideHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 135194987-(3-Phthalimidopropoxy)-tetralone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Hydroxy-1-tetralone (33.3 g) is dissolved in dimethylformamide (325 ml) and the mixture is cooled in an ice bath. Sodium methoxide (11.07 g) is added to the mixture. After the mixture is stirred for 3 min., N-(3-bromopropyl) phthalimide (54.96 g) is added to the mixture; stirring is continued and the reaction mixture stirred overnight. The resulting mixture is poured into H2O (650 ml), stirred for 1 hour, filtered, washed with H2O and air dried. The resulting fluffy near-white solid (62.8 g) is crystallized from ethyl acetate to give the desired product, a fluffy white solid (M.P. 149°-150° C. )

Workup

  1. temperaturethe mixture is cooled in an ice bath
  2. stirringstirring
  3. stirringthe reaction mixture stirred overnight
  4. stirringstirred for 1 hour
  5. filtrationfiltered
  6. washwashed with H2O and air
  7. customdried
  8. customThe resulting fluffy near-white solid (62.8 g) is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9ea8725c551f44b18bf8d2996ca1ab82
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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