HCID 14474494, compound → HCID 14474497, compound

HRID 1709615Notes

Reaction equation

HRID 1709615 reaction equation
[OH:1][CH:2]1[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][C:6]([CH:14](OC)[O:15]C)=[CH:7][CH:8]=2)[C:3]1([CH3:20])[CH3:19]>S(=O)(=O)(O)O.O>[CH:14]([C:6]1[CH:5]=[C:4]2[C:9]([C:10]([CH3:13])([CH3:12])[CH2:11][CH:2]([OH:1])[C:3]2([CH3:19])[CH3:20])=[CH:8][CH:7]=1)=[O:15]

Participants

4

Reactant 1

HCID 14474494HCID 14474494, compound

Product 1

HCID 14474497HCID 14474497, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

360 g of water and 0.5 g of concentrated sulfuric acid are initially taken, and 120 g of 1,2,3,4-tetrahydro-2-hydroxy-7-dimethoxymethyl-1,1,4,4-tetramethylnaphthalene are added. The mixture is then heated to the reflux temperature and the methanol is distilled off. The organic phase is taken up with methyl tert-butyl ether. The methyl tert-butyl ether phase is separated off, the methyl tert-butyl ether is distilled off and the residue is crystallized using petroleum ether/toluene. 89 g of 7-formyl-1,2,3,4-tetrahydro-2-hydroxy-1,1,4,4-tetramethylnaphthalene (mp. 76°-78° C.) are obtained. The product obtained was characterized by 1H-NMR. 1H-NMR (250 MHz, CDCl3): δ=1.23(s,3H), 1.37(s,3H), 1.41(s,3H), 1.50(s,1H), 1.83(dd, J1 =12Hz, J2 =4Hz,1H), 1.97(t,J=12Hz,1H), 2.83(sbr.,1H), 3.95(dd,J1 =12Hz, J2 =4Hz,1H), 7.52(d,J=8Hz, 1H), 7.73(d,J=8Hz,1H), 7.97 (s,1H), 10.03(s,1H)

Workup

  1. temperatureThe mixture is then heated to the reflux temperature
  2. distillationthe methanol is distilled off
  3. customThe methyl tert-butyl ether phase is separated off
  4. distillationthe methyl tert-butyl ether is distilled off
  5. customthe residue is crystallized

Sources & evidence

ORD record
ord-cd19da6c1c1f49b99b7ab6961da22a11
Source dataset
uspto-grants-1990_08
Patent number
US04950369

Reaction notes

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