Sulfuric Acid → 8-Methylsulfonyl-11-(1-hydroxycyclohexyl)-10-undecynoic acid

HRID 263012

Reaction equation

HRID 263012 reaction equation
[C:1]([C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].C([O:13][C:14](=[O:16])[CH3:15])(=O)C.[S:17](=[O:21])(=O)(O)[OH:18].C(O[C:26]1([C:32]#[CH:33])C[CH2:30][CH2:29][CH2:28][CH2:27]1)(=O)C.[CH3:34]COCC>>[CH3:34][S:17]([CH:32]([CH2:33][C:2]#[C:1][C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:15][C:14]([OH:13])=[O:16])(=[O:21])=[O:18]

Participants

6

Reactant 5

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 65251-EthynylcyclohexanolHCID 7918Acetic AnhydrideHCID 78903Cyclohexanol, 1-ethynyl-, 1-acetate

Product 1

HCID 213175308-Methylsulfonyl-11-(1-hydroxycyclohexyl)-10-undecynoic acid

Procedure

1-Ethynylcyclohexan-1-ol(100 g., 0.8 mole) is added dropwise with stirring to a mixture of acetic anhydride (86.7 g., 0.85 mole) and sulfuric acid (0.25 ml.). The temperature of the reaction mixture is kept at 10°-12° C. during the addition by means of an ice bath. The mixture is then stirred without cooling for 1.5 hours. It is then poured into 300 ml. of ice water. The oily product is taken up in ether, washed with water, dilute sodium bicarbonate solution and brine and dried over sodium sulfate. Distillation affords 107 g. (80%) of 1-acetoxy-1-ethynylcyclohexane, b.p. 95°-97° C./15 mm.

Workup

  1. additionThe temperature of the reaction mixture is kept at 10°-12° C. during the addition by means of an ice bath
  2. temperaturewithout cooling for 1.5 hours
  3. additionIt is then poured into 300 ml
  4. washwashed with water, dilute sodium bicarbonate solution and brine
  5. dry with materialdried over sodium sulfate
  6. distillationDistillation
  7. customaffords 107 g

Sources & evidence

ORD record
ord-6d4234a4f9e34d6e9bf746e354cc576a
Source dataset
uspto-grants-1979_05
Patent number
US04155908

Linked notes

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