Succinic Acid → Bis[(4-methylcyclohex-3-en-1-yl)methyl] butanedioate

HRID 33609

Reaction equation

HRID 33609 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH:3]=1.[C:10]1([CH3:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:17]([OH:24])(=O)[CH2:18][CH2:19][C:20]([OH:22])=[O:21].O.[C:26]1(C)C(S(O)(=O)=O)=CC=CC=1>O>[CH3:1][C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][C:17](=[O:24])[CH2:18][CH2:19][C:20]([O:22][CH2:16][CH:10]2[CH2:15][CH2:14][C:13]([CH3:26])=[CH:12][CH2:11]2)=[O:21])[CH2:4][CH:3]=1

Participants

6

Reactant 4

HCID 1110Succinic AcidHCID 1140TolueneHCID 5646723-Cyclohexene-1-methanol, 4-methyl-HCID 124969952-Methylbenzenesulfonic acid hydrate

Product 1

HCID 69305714Bis[(4-methylcyclohex-3-en-1-yl)methyl] butanedioateYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Added to 284 g (being 2 mol) of 4-methyl-3-cyclohexenylmethanol and one liter toluene solution containing 10 g (being 1 mol) of succinic acid anhydrate, was 5 g of toluenesulfonic acid monohydrate, and allowed to react for 8 hours at 110-120° C., while any generated water was removed using a water separating apparatus. After the reacted solution was washed with sodium bicarbonate water, distillation under reduced pressure was conducted to remove any toluene. The residual crude product was distilled under reduced pressure to obtain the objective compound. The yield was 90%.

Workup

  1. customwas removed
  2. washAfter the reacted solution was washed with sodium bicarbonate water, distillation under reduced pressure
  3. customto remove any toluene
  4. distillationThe residual crude product was distilled under reduced pressure
  5. customto obtain the objective compound

Sources & evidence

ORD record
ord-d8a7ba29005c42e5a62be1bcbb4d3711
Source dataset
uspto-grants-2008_09
Patent number
US07429622B2

Linked notes

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