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Hydrochloric Acid → 2,6-Bis(3-hydroxy-2,2-dimethylpropyl)naphthalene

HRID 462030
Notes
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Reaction equation

HRID 462030 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]([CH3:32])([CH3:31])[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][C:24]([CH3:30])([C:26](OC)=[O:27])[CH3:25])[CH:19]=2)[CH:14]=1)(OC)=[O:8].[NH4+].[Cl-].Cl>O1CCCC1.C(OCC)(=O)C>[OH:8][CH2:7][C:11]([CH3:32])([CH3:31])[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][C:24]([CH3:30])([CH3:25])[CH2:26][OH:27])[CH:19]=2)[CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 20314652HCID 20314652, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 213125812,6-Bis(3-hydroxy-2,2-dimethylpropyl)naphthaleneYield 59.3%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6.0 g of lithium aluminum hydride in 1 liter of dry tetrahydrofuran, 40 g of 2,6-bis(2-carbomethoxy-2-methylpropyl)naphthalene was added slowly. The reaction mixture thickened on stirring overnight. Then there was added 150 ml of ethyl acetate, 60 ml of saturated aqueous NH4Cl and 150 ml of concentrated HCl. After thorough mixing the solid and liquid were separated by filtration. The filtrate was evaporated to dryness and the residue was recrystallized from benzene to obtain about 20 g of 2,6-bis(3-hydroxy-2,2-dimethylpropyl)naphthalene. The solid from the above filtration was slurried with 50 ml of H2O, 10 ml of concentrated HCl and 50 ml of benzene and the mixture was heated at reflux for 1 hr. The benzene layer was separated, dried with MgSO4 at 80° C, filtered hot and then cooled to precipitate about 10 g of 2,6-bis(3-hydroxy-2,2-dimethylpropyl)naphthalene, m.p. 162°-165° C.

Workup

  1. additionAfter thorough mixing the solid and liquid
  2. customwere separated by filtration
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-fcbdb2f2cd604d629d42912004ce3865
Source dataset
uspto-grants-1977_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04065431

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes