Phenol → 5-Ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

HRID 1975789Notes

Reaction equation

HRID 1975789 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13].[Al+3].[Cl-].[Cl-].[Cl-].[C:18]1(O)C=CC=CC=1.[CH2:25](I)C.C(=O)([O-])[O-].[K+].[K+].C1(=O)C2C(=CC=CC=2)CCC1.[CH3:45][O:46][C:47]1[CH:56]=[CH:55][CH:54]=[C:53]2[C:48]=1[CH2:49][CH2:50][CH2:51][CH:52]2[C:57]([OH:59])=[O:58]>C1C=CC=CC=1.CC(C)=O>[CH2:1]([O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13])[CH3:18].[CH2:45]([O:46][C:47]1[CH:56]=[CH:55][CH:54]=[C:53]2[C:48]=1[CH2:49][CH2:50][CH2:51][CH:52]2[C:57]([OH:59])=[O:58])[CH3:25]

Participants

11

Reactant 7

HCID 996PhenolHCID 6340IodoethaneHCID 107241-TetraloneHCID 11430Potassium CarbonateHCID 366205-MethoxytetraloneHCID 6451240Aluminum(III) ChlorideHCID 107034695-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic Acid

Product 2

HCID 190984695-Ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acidHCID 218967975-Ethoxy-1-tetralone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 241BenzeneSolvent

Procedure

5-Ethoxy-1-tetralone was prepared from the commercially available 5-methoxy-1-tetralone by treatment with AlCl3 in benzene followed by alkylation of the resulting phenol with ethyl iodide in acetone in the presence of potassium carbonate. The resulting tetralone was then treated by the procedures described in International Patent Application Number WO 89/06645 for the preparation of 5-methoxy 1,2,3,4-tetrahydronaphthalene-1-carboxylic acid to yield 5-ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid. The title compound was prepared from 5-ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid by the procedures described in Example 10 through 15 to yield the product as a white solid. m.p. 219°-221° C. 1H NMR (DMSO-b6, 300 MHz) δ1.32 (t, 3H), 1.65-1.9 (m, 4H), 2.4-2.7 (m, 2H), 2.59 (s, 3H), 3.0-3.3 (m, 3H), 4.0 (m, 2H), 6.78 (d, 1H), 6.84 (d, 1H), 7.12 (t, 1H), 8.6 (bs, 2H).

Sources & evidence

ORD record
ord-d4a59f64970f428cb55a6067bb119372
Source dataset
uspto-grants-1994_02
Patent number
US05288749

Reaction notes

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