Tetralin → 5,6,7,8-Tetrahydro-1-naphthol

HRID 379363Notes

Reaction equation

HRID 379363 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[OH:11]N1C2C=CC=CC=2N=N1>CC(C)=O>[C:9]1(=[O:11])[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH2:6][CH2:7][CH2:8]1.[OH:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][CH2:2][CH2:1]2

Participants

5

Reactant 2

HCID 8404TetralinHCID 757711-Hydroxybenzotriazole

Product 2

HCID 107241-TetraloneYield 42%HCID 682585,6,7,8-Tetrahydro-1-naphtholYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

212 mg (1.60 mmol) of 1,2,3,4-tetrahydronaphthalene in 1.1 ml of acetone were reacted analogously to Example 1 with 71 mg (0.53 mmol) of 1-hydroxy-1H-benzotriazole in 3 ml of acetone and 15 ml of an aqueous solution of 2 mg/ml laccase from Trametes versicolor. After a reaction time of 24 hours, the reaction solution was extracted with chloroform and examined by NMR spectroscopy. Yield 42% of 1-tetralone and 6% of 5-hydroxytetralin (approx. 90% yield of 1-tetralone based on conversion).

Workup

  1. extractionAfter a reaction time of 24 hours, the reaction solution was extracted with chloroform

Sources & evidence

ORD record
ord-52eaba2c17794fdfb6bd6880d7ea211a
Source dataset
uspto-grants-2001_10
Patent number
US06297403B1

Reaction notes

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