m-Chloroperbenzoic acid → HCID 86734941, compound

HRID 259049Notes

Reaction equation

HRID 259049 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([O:20][CH2:21][CH2:22][CH:23]([CH:25]1[CH2:30][CH2:29][C:28]([CH3:31])=[CH:27][CH2:26]1)[CH3:24])(=[O:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]>C(Cl)Cl>[C:12]([O:20][CH2:21][CH2:22][CH:23]([CH:25]1[CH2:30][CH2:29][C:28]2([O:9][CH:27]2[CH2:26]1)[CH3:31])[CH3:24])(=[O:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 71366201Methyl 3-(4-methylcyclohex-3-en-1-yl)butyl butanedioate

Product 1

HCID 86734941HCID 86734941, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An 8.2g (0.04 mole) portion of 85% m-chloroperbenzoic acid was added portionwise over 15 min. to a stirred, cooled (0° C.) solution of 11.3g (0.04 mole) of succinic acid, 3-(4-methyl-3-cyclohexenyl)butyl methyl ester in 250 ml of methylene chloride. The temperature rose to 10° C. during the addition and to ambient after the cooling bath was removed. The reaction mixture was stirred overnight. Sufficient 5% sodium hydroxide was added to dissolve the precipitated acid, and the organic layer was separated, washed with 5% sodium hydroxide and with brine, dried over magnesium sulfate and concentrated. Obtained was 10.6g of succinic acid 3-(3,4-epoxy-4-methylcyclohexyl) butyl methyl ester as a clear, colorless liquid. The analytical determinations indicated that the product was pure and did not require further purification (See Table I).

Workup

  1. additionThe temperature rose to 10° C. during the addition
  2. customwas removed
  3. additionSufficient 5% sodium hydroxide was added
  4. dissolutionto dissolve the precipitated acid
  5. customthe organic layer was separated
  6. washwashed with 5% sodium hydroxide and with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customObtained
  10. custompurification (See Table I)

Sources & evidence

ORD record
ord-3497f0d1e68b41ac87a91ab5a861bb4a
Source dataset
uspto-grants-1977_07
Patent number
US04036629

Reaction notes

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