Ethylene Glycol → HCID 53963811, compound

HRID 267314Notes

Reaction equation

HRID 267314 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][C:8]([O:13][CH2:14][CH3:15])=[CH:7][C:6]=1[CH3:16])=[O:4].C(O)C[OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][C:8]2([O:19][CH2:15][CH2:14][O:13]2)[CH2:7][C:6]=1[CH3:16])=[O:4]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 53641044HCID 53641044, compound

Product 1

HCID 53963811HCID 53963811, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

670 g. of crude 2,6,6-trimethyl-4-ethoxy-1,3-cyclohexadien-1-carboxylic acid methyl ester and 185 g. of ethylene glycol were heated in 3 l. of benzene in the presence of 3 g. of p-toluene sulfonic acid. The reaction was stopped after 1.5 l. of benzene had distilled over. The cold solution was washed with sodium bicarbonate solution and water, dried, and evaporated. The remaining oil was dissolved in 1 l. of petroleum ether and crystallized at -10°. A yield of 320 g. (m.p. 67°-69°) was obtained after recrystallization from petroleum ether. This product was identified as 7,9,9-trimethyl-1,4-dioxaspiro[4,5]dec-7-on-8-carboxylic acid methyl ester.

Workup

  1. distillationof benzene had distilled over
  2. washThe cold solution was washed with sodium bicarbonate solution and water
  3. customdried
  4. customevaporated
  5. dissolutionThe remaining oil was dissolved in 1 l
  6. customof petroleum ether and crystallized at -10°
  7. custom(m.p. 67°-69°) was obtained
  8. customafter recrystallization from petroleum ether

Sources & evidence

ORD record
ord-ca8ec2c6a7b94f99afebfe1f2807ea5a
Source dataset
uspto-grants-1976_03
Patent number
US03941841

Reaction notes

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