Sulfuric Acid → 3-(4,4-Dimethyl-cyclohex-1-enyl)-propionic acid butyl ester

HRID 585465

Reaction equation

HRID 585465 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:12][CH2:11][C:5]2([O:9][C:8](=[O:10])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.OS(O)(=O)=O>C(O)CCC>[CH2:1]([O:9][C:8](=[O:10])[CH2:7][CH2:6][C:5]1[CH2:11][CH2:12][C:2]([CH3:13])([CH3:1])[CH2:3][CH:4]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 134091248,8-Dimethyl-1-oxa-spiro[4.5]decan-2-one

Product 1

HCID 236558383-(4,4-Dimethyl-cyclohex-1-enyl)-propionic acid butyl ester

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

The crude 8,8-dimethyl-1-oxa-spiro[4.5]decan-2-one (40.2 g, 0.22 mol) was introduced into a 250 ml three necked round bottom flask together with butanol (23 g) and concentrated H2SO4 (0.5 g). Temperature was risen to 140° C. and during 8 hours fresh butanol (42.9 g) was introduced, while collecting a mixture of butanol/water. The reaction mixture was cooled to room temperature and toluene (66 g) and water (66 g) were added. The organic phase was washed with NaHCO3 and water to yield after concentration 51.42 g of the desired compound. Flash distillation (68°–70° C., 0.2 hPa) led to 35.0 g of butylester (overall yield: 47%; GC purity: 96.0%).

Workup

  1. customwhile collecting
  2. additiona mixture of butanol/water
  3. additiontoluene (66 g) and water (66 g) were added
  4. washThe organic phase was washed with NaHCO3 and water

Sources & evidence

ORD record
ord-0d16dd0ef4a845798ff4baff7b4ef04d
Source dataset
uspto-grants-2005_08
Patent number
US06933265B2

Linked notes

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