Methanol → HCID 20496884, compound

HRID 1660057Notes

Reaction equation

HRID 1660057 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([CH3:10])=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([CH3:25])([CH3:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:13][C:12]=3[OH:26])[CH2:5]2)[O:3]C1.C(O)(=O)C(O)=O.CO.O>CCOCC>[CH3:25][C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:6]2[CH2:5][C:4](=[O:3])[CH2:9][CH2:8][C:7]=2[CH3:10])=[C:12]([OH:26])[CH:13]=1)([CH3:24])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 971Oxalic AcidHCID 57080245HCID 57080245, compound

Product 1

HCID 20496884HCID 20496884, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4.08 g. (0.1 mol.) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-methyl-cyclohex-3-enone ethylene ketal, 50 ml. of 2 N oxalic acid and 50 ml. of methanol was stirred at 25° C. for 6 hours. The reaction mixture was added to 500 ml. of water-250 ml. of ether. The ether extract was washed once with 250 ml. of saturated sodium bicarbonate, once with 250 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue was purified via column chromatography on 400 g. of silica gel eluted with 50% ether-pentane to yield the title compound.

Workup

  1. additionA mixture of 4.08 g
  2. additionThe reaction mixture was added to 500 ml
  3. extractionThe ether extract
  4. washwas washed once with 250 ml
  5. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified via column chromatography on 400 g
  8. washof silica gel eluted with 50% ether-pentane

Sources & evidence

ORD record
ord-a891b3aff63b4995bebd755bfdcb3510
Source dataset
uspto-grants-1981_12
Patent number
US04306097

Reaction notes

Loading…