Dichloromethane → 11-Phenyl-1-undecanol O-methanesulfonate

HRID 2052480Notes

Reaction equation

HRID 2052480 reaction equation
ClCCl.[C:4]1([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(N(CC)CC)C>[CH3:22][S:23]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 11651716Benzeneundecanol

Product 1

HCID 1307969911-Phenyl-1-undecanol O-methanesulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 750 ml. of dichloromethane, 37.2 g. of 11-phenyl-1-undecanol (prepared as described in Example 6) and 32 ml. of triethylamine cooled in an ice-salt bath to -10° C. is added dropwise, over 15 minutes, 13.2 ml. of methanesulfonyl chloride. The mixture is cooled at -10° C. to -15° C. for 30 minutes and then washed with 300 ml. of cold water, 300 ml. of cold 10% hydrochloric acid, 300 ml. of cold 5% sodium carbonate and with 200 ml. of cold, saturated, sodium chloride solution. The organic layer is dried over magnesium sulfate and concentrated in vacuo to give a pale yellow oil.

Workup

  1. additionTo a mixture of 750 ml
  2. additionis added dropwise, over 15 minutes
  3. temperatureThe mixture is cooled at -10° C. to -15° C. for 30 minutes
  4. washwashed with 300 ml
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a pale yellow oil

Sources & evidence

ORD record
ord-6c34a45dc8c349abb9fedd431631ee88
Source dataset
uspto-grants-1980_01
Patent number
US04185115

Reaction notes

Loading…