Methanol → HCID 20496884, compound

HRID 1074477Notes

Reaction equation

HRID 1074477 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-672d07029bd8451cb36c3ec1fd8b109e
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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