Acetic Acid → 6-Methoxy-alpha-tetralone

HRID 1529843Notes

Reaction equation

HRID 1529843 reaction equation
[CH2:1]1[CH:10]([OH:11])[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=CC=2)[CH2:2]1.N[C:13](N)=S.[C:16]([OH:19])(=O)[CH3:17]>C(OCC)C>[CH3:13][O:11][C:10]1[CH:1]=[C:2]2[C:17](=[CH:8][CH:9]=1)[C:16](=[O:19])[CH2:5][CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 107471,2,3,4-Tetrahydro-2-naphthalenolHCID 2723790Thiourea2×

Product 1

HCID 141126-Methoxy-alpha-tetralone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At 0° C., to a stirred mixture of crude tetralol 46 (269 g, 1.32 mol) and thiourea (100 g, 1.32 mol) was added 370 mL of glacial acetic acid. The reaction mixture was stirred at rt for approximatively 1 h. When thiourea was completely dissolved, the reaction mixture was poured in diethyl ether (8 L), stirred for 2 h and the precipitated salt was filtered to afford 285 g (62% from 6-methoxy-1-tetralone) of compound 47. 1H NMR (400 MHz, acetone-d6) δ 1.82 (m, 2H), 1.89 (s, 3H), 2.61 (m, 2H), 2.77 (m, 2H), 3.77 (s, 3H), 3.86 (d, J=7.8 Hz, 2H), 6.04 (m, 1H), 6.69 (m, 1H), 6.75 (m, 1H), 7.56 (d, J=8.8 Hz, 1H) ppm (described in JOC, 33, 3126 (1968)).

Workup

  1. stirringstirred for 2 h
  2. filtrationthe precipitated salt was filtered

Sources & evidence

ORD record
ord-263708bd5fd0461d8d2b7d315f343f80
Source dataset
uspto-grants-2015_07
Patent number
US09090651B2

Reaction notes

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