Sulfuric Acid → 8-Acetyl-11-(1-hydroxycyclohexyl)undec-10-ynoic acid

HRID 372902Notes

Reaction equation

HRID 372902 reaction equation
[C:1]([C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].[C:10]([O:13]C(=O)C)(=[O:12])C.S(=O)(=O)(O)O.C(O[C:26]1([C:32]#[CH:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)(=O)C.[CH3:34][CH2:35][O:36]CC>>[C:35]([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][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:10]([OH:13])=[O:12])(=[O:36])[CH3:34]

Participants

6

Reactant 5

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

Product 1

HCID 203222738-Acetyl-11-(1-hydroxycyclohexyl)undec-10-ynoic 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° 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°/15 mm.

Workup

  1. additionThe temperature of the reaction mixture is kept at 10°-12° 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-f09ec884ccbd44e5bdede3a7ea5bf91e
Source dataset
uspto-grants-1978_05
Patent number
US04092356

Reaction notes

Loading…