Hydrochloric Acid → HCID 20239859, compound

HRID 364771Notes

Reaction equation

HRID 364771 reaction equation
[CH:1]([C:3]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]2[C:9]([CH3:16])([CH3:15])[CH2:8][CH2:7][C:6]([CH3:18])([CH3:17])[C:5]=2[C:4]=1[OH:19])=[O:2].[OH-].[K+].S(OC)(O[CH3:26])(=O)=O.Cl>C1(C)C=CC=CC=1>[CH:1]([C:3]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]2[C:9]([CH3:15])([CH3:16])[CH2:8][CH2:7][C:6]([CH3:18])([CH3:17])[C:5]=2[C:4]=1[O:19][CH3:26])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 20239855HCID 20239855, compound

Product 1

HCID 20239859HCID 20239859, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

Methylation. 2-Formyl-1-hydroxy-3,4,5,5,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalene (8.7 g, 0.0335 mol) was stirred with toluene (60 mL), and potassium hydroxide 85% (3.1 g, 0.047 mol) was added in one portion. The mixture was heated to 55° C., dimethyl sulfate (6.3 g, 0.05 mol) added during 0.5 h at 55°-60° C., and the heating continued at 55°-60° C. for 4 h. The mixture was cooled to 20° C., neutralized with 5% hydrochloric acid, then washed with water (10 mL), and finally washed with brine (10 mL). The solvent was removed by distillation and the residue distilled to give 2-formyl-1-methoxy-3,4,5,5,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalene (5.8 g), GLC purity 97%. Crystallization from hexane gave 3.5 g material with GLC purity 100%. 1H-NMR (CDCl3) δ10.40 (1H, s), 3.78 (3H, s), 2.40 (3H, s), 2.37 (3H, s), 1.64 (4H, s), 1.45 (6H, s), 1.42 (6H, s). 13C-NMR (CDCl3) δ193.5 (1C, d), 162.9 (1C, s), 151.6 (1C, s), 137.7 (1C, s), 136.7 (1C, s), 132.5 (1C, s), 126.9 (1C, s), 65.7 (1C, q), 40.3 (1C, t), 38.2 (1C, t), 36.2 (1C, s), 35.2 (1C, s), 30.2 (2C, q), 29.8 (2C, q), 19.7 (1C, q), 15.8 (1C, q). IR (KBr) 1244, 1271, 1682 cm-1, MS (m/e) 274.2 (M+, 34.9), 259.1 (100.0), 260.2 (21.7), 189.1 (21.5).

Workup

  1. additionwas added in one portion
  2. temperatureThe mixture was cooled to 20° C.
  3. washwashed with water (10 mL)
  4. washfinally washed with brine (10 mL)
  5. customThe solvent was removed by distillation
  6. distillationthe residue distilled

Sources & evidence

ORD record
ord-93db5759ebac43a8affdf4b723adeabd
Source dataset
uspto-grants-1986_08
Patent number
US04605778

Reaction notes

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