Water → HCID 13519498, compound

HRID 280142Notes

Reaction equation

HRID 280142 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 13519498HCID 13519498, compound

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-64b00036f00c41938961949f3d284e48
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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