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Hydrochloric Acid → 2-(Bis(4-hydroxyphenyl)methyl)benzenemethanol

HRID 1659600
Notes
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Reaction equation

HRID 1659600 reaction equation
[CH:1]1[CH:6]=[C:5]([CH:7]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[C:4]([C:22](O)=[O:23])=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OC(=O)C)C.Cl>O1CCCC1.C(OCC)C.O>[CH:2]1[CH:3]=[C:4]([CH2:22][OH:23])[C:5]([CH:7]([C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:6][CH:1]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 66494PhenolphthalinHCID 21226445Aluminium lithium hydride

Product 1

HCID 664952-(Bis(4-hydroxyphenyl)methyl)benzenemethanol

Reagents, catalysts & solvents 3

HCID 962Water
Solvent
HCID 3283Diethyl EtherSolvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.5 g of the methyl ester of phenolphthalin prepared in step (ii) dissolved in 30 ml dry tetrahydrofuran was slowly added to a suspension of 0.5 g of lithium aluminum hydride in 20 ml dry tetrahydrofuran. The resulting reaction mixture was heated at reflux for 30 minutes, and then excess ethylacetate was added. The reaction mixture was poured into 1N HCl, extracted with two 200 ml portions of ethyl ether and the ether evaporated leaving a residue of solid and some water. The residue was taken up in ethyl ether and the ether decanted from water, dried over sodium sulfate, filtered and the solvent removed in vacuo to give 0.42 g of phenolphthalol as a white solid. TLC on silica gel using ether showed the title compound as one major spot, and nmr was consistent with the phthalol structure.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 30 minutes
  4. extractionextracted with two 200 ml portions of ethyl ether
  5. customthe ether evaporated
  6. customleaving a residue of solid
  7. customthe ether decanted from water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f3b9452b2b9246139e0df222cf46acbe
Source dataset
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04304833

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes