Acetic Acid → 3-Ethyl-1-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxaldehyde

HRID 1979894Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]([OH:17])[C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1)[CH3:2].[C:18](O)(=[O:20])C.C1N2CN3CN(C2)CN1C3.O>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[C:4]([CH:18]=[O:20])=[C:5]([OH:17])[C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1)[CH3:2]

Participants

Conditions

Temperature: 95 °C

Procedure

3-Ethyl-1-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (94 g, 0.405 mol) was stirred with glacial acetic acid (670 mL), and hexamethylenetetramine (102.6 g, 0.73 mol) was added in one portion. The mixture was heated at 95° C. for 3 h, hot water (670 mL) added, and the heating was continued for an additional 1.5 h at 100° C. The mixture was cooled to 20° C., toluene (200 mL) was added, and the mixture was stirred vigorously. The organic layer was separated, washed with water (3×150 mL), then neutralized with 5% NaHCO3 solution, and finally washed with brine (50 mL). The solvent was evaporated and the residue distilled to give 3-ethyl-1-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxaldehyde (77.9 g), bp 127°-132° C./0.5 mm, GLC purity 98%, exhibiting the expected spectral data.

Workup

additionwas added in one portion
temperatureThe mixture was cooled to 20° C.
customThe organic layer was separated
washwashed with water (3×150 mL)
washfinally washed with brine (50 mL)
customThe solvent was evaporated
distillationthe residue distilled

Sources & evidence

ORD record: ord-e1f05fc22f664ceeb932b3dd9da3184e
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04483786

Reaction notes

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