Water → HCID 14236873, compound

HRID 2290540Notes

Reaction equation

HRID 2290540 reaction equation
[OH:1][CH2:2][C:3]1([CH2:8][OH:9])[CH2:5][CH:4]1[CH:6]=[CH2:7].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH2:19]>N1C=CC=CC=1.C1CCCCC1.CCOC(C)=O>[C:10]([O:1][CH2:2][C:3]1([CH2:8][O:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5][CH:4]1[CH:6]=[CH2:7])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 13572991(2-Ethenylcyclopropane-1,1-diyl)dimethanol

Product 1

HCID 14236873HCID 14236873, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

A solution of 5.5 g (43 mmoles) of 1,1-bis(hydroxymethyl)-2-vinylcyclopropane in 40 ml of pyridine was cooled to 0° and 18.5 g (130 mmoles; 15.2 ml) of benzoyl chloride was added dropwise over 15 minutes. The mixture was stirred at 22° for 2 hours. TLC in cyclohexane-EtOAc (4:1) indicated that the reaction was complete. The reaction mixture was treated with 8 ml of water and stirred at 22° for 20 hours. It was concentrated to a residual oil and redissolved in 150 ml of EtOAc and washed with 50 ml of water, three 50-ml portions of 2N HCl, four 50 ml portions of saturated NaHCO3, dried (MgSO4), filtered and concentrated to give 11 g (75%) of the title compound, Rf cyclohexane-ethyl acetate (4:1) 0.7.

Workup

  1. stirringstirred at 22° for 20 hours
  2. concentrationIt was concentrated to a residual oil
  3. dissolutionredissolved in 150 ml of EtOAc
  4. washwashed with 50 ml of water, three 50-ml portions of 2N HCl, four 50 ml portions of saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf8dcf6ad07a470998ba09521c185463
Source dataset
uspto-grants-1986_10
Patent number
US04617304

Reaction notes

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