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Hydrochloric Acid → 6-Benzoxazoleethanol, beta-methyl-2-phenyl-

HRID 1658083
Notes
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Reaction equation

HRID 1658083 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[O:14][C:15]3[CH:21]=[C:20]([CH:22]([CH3:28])[C:23](OCC)=[O:24])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C.Cl>CCOCC>[C:7]1([C:13]2[O:14][C:15]3[CH:21]=[C:20]([CH:22]([CH3:28])[CH2:23][OH:24])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 12370785HCID 12370785, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 399496-Benzoxazoleethanol, beta-methyl-2-phenyl-

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent
2×

Procedure

A solution of lithium aluminium hydride (~ 2 gm) in ether (50 ml) was slowly added to a solution of ethyl 2-(2-phenyl-6-benzoxazolyl)-propionate (5 g) in ether (40 ml). The mixture was heated under reflux for 1 hr., then ethyl acetate was slowly added until effervescence ceased. 6-N-Aqueous hydrochloric acid was then added and the ether layer was separated off and dried. Chromatography over silica gel yield pure 2-(2-phenyl-6-benzoxazolyl)-propanol, m.p. 98°C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. customthe ether layer was separated off
  4. customdried

Sources & evidence

ORD record
ord-561ad85614d24c0383358fba13dbdef7
Source dataset
uspto-grants-1976_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03962441

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes