Acetic Acid → 6-Chloromethyl-1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene

HRID 486419

Reaktionsgleichung

Reaktionsgleichung von HRID 486419
[CH:1]([C:3]1[C:4]([O:18][CH3:19])=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9]([CH3:15])([CH3:14])[CH2:8][CH2:7][C:6]2([CH3:17])[CH3:16])=O.CC1(C)C2C(=C(OC)C=C(C)C=2)C(C)(C)CC1.C(O)(=O)C.P(=O)(O)(O)O.[ClH:46].C=O>C1C=CC=CC=1>[Cl:46][CH2:1][C:3]1[C:4]([O:18][CH3:19])=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9]([CH3:15])([CH3:14])[CH2:8][CH2:7][C:6]2([CH3:17])[CH3:16]

Komponenten

8

Edukt 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1004Phosphoric AcidHCID 1747662-Naphthalenecarboxaldehyde, 5,6,7,8-tetrahydro-1-methoxy-3,5,5,8,8-pentamethyl-HCID 2267025-Methoxy-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 190951706-Chloromethyl-1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To prepare the corresponding 6-carboxaldehyde, 6-formyl-1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene, 1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene (23.2 g, 0.1 mol) is added to a stirred solution of acetic acid (18.2 g, 0.3 mol), 85% phosphoric acid (17.6 g, 0.15 mol), hydrochloric acid (28.7 g, 0.3 mol) and paraformaldehyde (7.3 g, 0.24 mol). The mixture is stirred and heated at 95° C. for 16 hr. The reaction mixture is then cooled to 25° C., benzene (50 ml) added, and stirred vigorously. The organic layer is separated, washed with water (2×25 ml), neutralized with 5% sodium bicarbonate solution, and dried (Na2SO4). The solvent is removed by distillation to provide 6-chloromethyl-1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene.

Aufarbeitung

  1. temperatureThe reaction mixture is then cooled to 25° C.
  2. stirringstirred vigorously
  3. customThe organic layer is separated
  4. washwashed with water (2×25 ml)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is removed by distillation

Quellen und Nachweise

ORD-Eintrag
ord-b855dfe161b34b50b9fc74599a97f95a
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292719

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