Benzyl Bromide → HCID 86747691, compound

HRID 2379024Notes

Reaction equation

HRID 2379024 reaction equation
S([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([O:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23](S(O)(=O)=O)=[CH:22][CH:21]=2)=[O:19])=[O:16])=[CH:7][CH:6]=1)(O)(=O)=O.[K].[OH-:35].[K+].[C:37](=[O:40])([O-])[O-].[K+].[K+].[CH2:43](Br)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>>[CH2:43]([O:35][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([O:17][C:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([O:40][CH2:37][C:5]3[CH:14]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:22][CH:21]=2)=[O:19])=[O:16])=[CH:7][CH:6]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 5

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 57149178HCID 57149178, compound

Product 1

HCID 86747691HCID 86747691, compound

Procedure

4-sulfonaphthalic anhydride (Orlex Chemical Corp., Fairlawn, N.J.) or the corresponding potassium salt (Aldrich Chemical Co., Milwaukee, Wis.) is fused with molten potassium hydroxide, cooled, and acidified. The resulting 4-hydroxynaphthalic anhydride is removed by filtration and treated with one equivalent of potassium carbonate and benzyl bromide to obtain 4-benzyloxy naphthalic anhydride. Lithium tetrahydride aluminate (lithium aluminum hydride) reduction in tetrahydrofuran for 3 h at reflux temperatures gives the 1-8-naphthalenedimethanol. A suspension of the dimethanol (1.3 g, 5.0 mmol) in toluene (15 ml) is treated with a solution of phosphorous bromide (0.7 ml, 0.2 g, 7.5 mmol) in methylene chloride (7.5 ml) during 20-30 minutes and reacted for an hour. The solution is poured into ice-water, diluted with ethyl acetate, partitioned, and the organics are washed with 5% sodium chloride solutions. Drying and evaporation of solvent gives a crystalline residue (1.94 g) which deposits 1,8-dibromomethylene-4-benzyloxynaphthalene (1.3 g, m.p. 59°-60° C.) from hexane solution.

Workup

  1. temperaturecooled
  2. customThe resulting 4-hydroxynaphthalic anhydride is removed by filtration

Sources & evidence

ORD record
ord-51a2af66a65a414cad0d653987a80841
Source dataset
uspto-grants-1994_11
Patent number
US05360797

Reaction notes

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