2,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene)cyclohexanone → Cyclovalone

HRID 714193Notes

Reaction equation

HRID 714193 reaction equation
COC[O:4][C:5]1[CH:31]=[CH:30][C:8]([CH:9]=[C:10]2[CH2:15][CH2:14][CH2:13][C:12](=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23]COC)=[C:19]([O:27][CH3:28])[CH:18]=3)[C:11]2=[O:29])=[CH:7][C:6]=1[O:32][CH3:33]>CO.Cl>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([CH:16]=[C:12]2[CH2:13][CH2:14][CH2:15][C:10](=[CH:9][C:8]3[CH:30]=[CH:31][C:5]([OH:4])=[C:6]([O:32][CH3:33])[CH:7]=3)[C:11]2=[O:29])=[CH:18][C:19]=1[O:27][CH3:28]

Participants

4

Reactant 1

HCID 695017962,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene)cyclohexanone

Product 1

HCID 11366CyclovaloneYield 66%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

2,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene) cyclohexanone (38j, 0.49 g, 1.1 mmol) was dissolved in methanol (100 ml) and stirred for 15 min at room temperature. Concentrated hydrochloric acid (3 drops) was added and the mixture stirred for 3 hr at 60° C. The methanol was evaporated and the resulting residue extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethanol to give 0.26 g (66%) of a yellow solid: mp 177-178° C. [expected mp 179-181° C.]; 1H NMR: δ 1.79 (m, 2H), 2.90 (t, 4H, J=5.4 Hz), 3.89 (s, 6H), 5.88 (s, 2H), 6.91 (s, 2H), 6.96 (d, 2H, J=4.8 Hz), 7.06 (d, 2H, J=8.0 Hz), 7.72 (s, 2H); 13C NMR: δ 23.1, 28.5, 56.0, 113.2, 114.4, 124.4, 128.5, 134.2, 136.9, 146.2, 146.4, 172.8.

Workup

  1. stirringthe mixture stirred for 3 hr at 60° C
  2. customThe methanol was evaporated
  3. extractionthe resulting residue extracted into ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a solid
  9. customThe crude solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-5535482734a54a599f5616e70189911a
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Reaction notes

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