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Tetrahydrofuran → 4-[3-Hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzenemethanol

HRID 861789
Notes
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Reaction equation

HRID 861789 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][CH:14]([OH:29])[C:15]2[CH:24]=[CH:23][C:22]3[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=3[CH:16]=2)=[CH:8][CH:7]=1)(=O)C.C1COCC1.[OH-].[Na+]>O>[OH:29][CH:14]([C:15]1[CH:24]=[CH:23][C:22]2[C:21]([CH3:26])([CH3:25])[CH2:20][CH2:19][C:18]([CH3:28])([CH3:27])[C:17]=2[CH:16]=1)[C:13]#[C:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 226194414-[3-Hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzyl acetate

Product 1

HCID 542569824-[3-Hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzenemethanol

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

780 mg (2 mmol) of 4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzyl acetate and 30 ml of THF were introduced into a round-bottomed flask. 5 ml of a 2N methanolic sodium hydroxide solution were added and stirring was carried out for 30 min. The reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was triturated in heptane and filtered, 419 mg (60%) of the expected compound, with a melting point of 85°-86° C., were recovered.

Workup

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas triturated in heptane
  7. filtrationfiltered
  8. custom419 mg (60%) of the expected compound, with a melting point of 85°-86° C., were recovered

Sources & evidence

ORD record
ord-a99b049535f148d6860b22b509ccfaf9
Source dataset
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05716624

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes