Succinic Acid → HCID 14770397, compound

HRID 1722636Notes

Reaction equation

HRID 1722636 reaction equation
[OH:1][C:2]1[C:3]([CH3:24])=[C:4]([CH3:23])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH:7]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[C:6]=2[C:21]=1[CH3:22].[C:25](O)(=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29].S(=O)(=O)(O)O>C(OCCCC)CCC>[CH:18]([C:15]1[CH:16]=[CH:17][C:12]([CH:7]2[C:6]3[C:21]([CH3:22])=[C:2]([O:1][C:25]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:31])[C:3]([CH3:24])=[C:4]([CH3:23])[C:5]=3[O:9][C:8]2([CH3:10])[CH3:11])=[CH:13][CH:14]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 1110Succinic AcidHCID 1118Sulfuric AcidHCID 10881888HCID 10881888, compound

Product 1

HCID 14770397HCID 14770397, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Procedure

To a solution of 2.0 g (6.16 m mol) of 5-hydroxy-2,2,4,6,7 -pentamethyl-3-(4-isopropylphenyl)-2,3-dihydrobenzofuran obtained in Example 20 in 10 ml of dibutyl ether were added 740 mg (7.4 m mol) of anhydrous succinic acid and 0.1 ml of conc. sulfuric acid. This was stired at 80° C. for 1 hour. After cooling, the reaction mixture was washed with water, dried and concentrated. The resulting residue was purified by silica gel chromatography (eluted by isopropyl ether). Addition of isopropyl ether-hexane to the resulting concentrate gave 620 mg (yield 23.7%) of 3[3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yloxycarbonyl]propionic acid. mp. 141°-142° C.

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel chromatography (eluted by isopropyl ether)
  6. additionAddition of isopropyl ether-hexane to the resulting
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-969a6fc02ca64f92828434339b6c903b
Source dataset
uspto-grants-1989_08
Patent number
US04857516

Reaction notes

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