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Hydrochloric Acid → HCID 18348681, compound

HRID 2268465
Notes
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Reaction equation

HRID 2268465 reaction equation
[BH4-].[Na+].CO.[CH3:5][O:6][C:7]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[C:13]([O:20][CH3:21])=[C:12]2[C:8]=1[CH2:9][CH:10]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)[C:11]2=[O:22].Cl>O>[OH:22][CH:11]1[C:12]2[C:8](=[C:7]([O:6][CH3:5])[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[C:13]=2[O:20][CH3:21])[CH2:9][CH:10]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 18348616HCID 18348616, compound

Product 1

HCID 18348681HCID 18348681, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

Sodium borohydride (254 mg, 6.72 mmols) was added to a methanol (15 ml) solution of methyl 4-[4-(4,5,6,7-tetramethoxyindan-1-on-2-yl)butoxy]benzoate (1.54 g, 3.36 mmols), with cooling with ice, and then the mixture allowed to warm to room temperature, and stirring was continued for 6 hours. Water was added to the reaction mixture, which was then neutralized with hydrochloric acid added thereto, and thereafter extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo to obtain methyl 4-[4-(1-hydroxy-4,5,6,7-tetramethoxyindan-2-yl)butoxy]benzoate (1.50 g).

Workup

  1. temperaturewith cooling with ice
  2. additionadded
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and then dried
  6. customThe solvent was evaporated out in vacuo

Sources & evidence

ORD record
ord-09cf008764b0440595effde9a6172a4c
Source dataset
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06326369B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes