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Hydrochloric Acid → 4-(3,4-Dihydroxy-5-nitrophenyl)-3-methylbut-3-en-2-ol

HRID 1974692
Notes
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Reaction equation

HRID 1974692 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH3:17])[C:14](=[O:16])[CH3:15])[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].[BH4-].[Na+].O.Cl>[OH-].[Na+]>[OH:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH3:17])[CH:14]([OH:16])[CH3:15])[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 540099494-(3,4-Dihydroxy-5-nitrophenyl)-3-methylbut-3-en-2-one

Product 1

HCID 544528424-(3,4-Dihydroxy-5-nitrophenyl)-3-methylbut-3-en-2-ol

Reagents, catalysts & solvents 1

HCID 14798
Sodium Hydroxide
Solvent

Procedure

1.8 g of the product obtained in Example 6 was dissolved in 20 ml of 1N NaOH-solution and 4.0 g of sodium borohydride in small amount of water was added. The mixture was stirred over night at room temperature, acidified with hydrochloric acid and extracted with ether. The solvent was evaporated in vacuo and the residue purified in a silica gel column by using toluene-acetic acid dioxane (18:1:1). The product was crystallized from dichloromethane petroleum ether. Yield 0.80 g (44%), m.p. 102°-104° C.

Workup

  1. extractionextracted with ether
  2. customThe solvent was evaporated in vacuo
  3. customthe residue purified in a silica gel column
  4. customThe product was crystallized from dichloromethane petroleum ether

Sources & evidence

ORD record
ord-6531417258de4b3b934cbb86440db8d6
Source dataset
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05283352

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes