Hydrochloric Acid → (+)-2,2-Dibutyl-5-(2-quinolylmethoxy)-1,2,3,4-tetrahydro-1-naphthol hydrochloride

HRID 1650223Notes

Reaction equation

HRID 1650223 reaction equation
[CH2:1]([C:5]1([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:6]1[OH:27])[CH2:2][CH2:3][CH3:4].[ClH:32]>C(OCC)(=O)C>[ClH:32].[CH2:1]([C:5]1([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:6]1[OH:27])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 164102FR 110302

Product 1

HCID 19990531(+)-2,2-Dibutyl-5-(2-quinolylmethoxy)-1,2,3,4-tetrahydro-1-naphthol hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (+)-2,2-dibutyl-5-(2-quinolylmethoxy)-1,2,3,4-tetrahydro-1-naphthol (14.5 g) in ethyl acetate (145 ml) was added 3N-hydrogen chloride solution in ethyl acetate (20 ml) in one portion with vigorous stirring at ambient temperature. After stirring for 20 minutes, the precipitates were collected by filtration and washed with ethyl acetate. The pale yellow solid was recrystallized from acetonitrile to yield (+)-2,2-dibutyl-5-(2-quinolyl- methoxy)-1,2,3,4-tetrahydro-1-naphthol hydrochloride (11.605 g) as white solid. mp: 138°-140° C. [α]D25 +6 9° (c=0.62, MeOH). NMR (CD3OD, δ): 0.88 (3H, t, J=6 Hz), 0.96 (3H, t, J=6 Hz), 1.10-1.90 (14H, m), 2.63 (1H, m), 2.91 (1H, m), 4.30 (1H, s), 5.71 (2H, s), 6.98.(1H, d, J=8 Hz), 7.08 (1H, d, J=8 Hz), 7.22 (1H, t, J=8 Hz), 8.00 (1H, t, J=8 Hz), 8.16-8.43 (4H, m), 9.22 (1H, d, J=8 Hz).

Workup

  1. stirringAfter stirring for 20 minutes
  2. filtrationthe precipitates were collected by filtration
  3. washwashed with ethyl acetate
  4. customThe pale yellow solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-4ce7ac4359ca45fba0c2d44b68ecc8f8
Source dataset
uspto-grants-1990_05
Patent number
US04923881

Reaction notes

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