Thionyl Chloride → 1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentyl Chloride

HRID 1390552Notes

Reaction equation

HRID 1390552 reaction equation
[CH3:1][C:2]1([CH3:24])[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[CH2:9][CH2:10][CH:11](O)[CH2:12][CH2:13][CH:14]1[C:19]([CH3:21])([CH3:20])[CH:18]2[CH2:22][CH:15]1[CH2:16][CH2:17]2.S(Cl)([Cl:27])=O>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:24])[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[CH2:9][CH2:10][CH:11]([Cl:27])[CH2:12][CH2:13][CH:14]1[C:19]([CH3:21])([CH3:20])[CH:18]2[CH2:22][CH:15]1[CH2:16][CH2:17]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 213328421,5-Di-(3,3-dimethylnorborn-2-yl)-3-pentanol

Product 1

HCID 213328401,5-di-(3,3-dimethylnorborn-2-yl)-3-pentyl Chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 16.6 gm. of 1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentanol in 25 ml. of dry pyridine is cooled to -10° C. There is then added with good agitation, 14.3 gm. of thionyl chloride over a 15 minute period. The solution is allowed to warm to room temperature and gradually heated over a period of 4 to 5 hours to 100° C. After an additional two hours at 100° C. the excess thionyl chloride is removed by vacuum stripping and the reside mixed with cracked ice. Three 100 ml. ether extractions are used to remove the halide, the diethyl ether extracts are washed with 4 × 200 ml. ice water, the ether layer separated, dried over anhydrous magnesium sulfate, filtered and stripped. The residue of di-substituted pentyl chloride may be further purified by distillation in vacuo or is suitable for further reaction as such.

Workup

  1. additionThere is then added with good agitation, 14.3 gm
  2. temperaturegradually heated over a period of 4 to 5 hours to 100° C
  3. customAfter an additional two hours at 100° C. the excess thionyl chloride is removed by vacuum stripping
  4. additionthe reside mixed with cracked ice
  5. extractionether extractions
  6. customto remove the halide
  7. washthe diethyl ether extracts are washed with 4 × 200 ml
  8. customice water, the ether layer separated
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. distillationThe residue of di-substituted pentyl chloride may be further purified by distillation in vacuo
  12. customis suitable for further reaction as such

Sources & evidence

ORD record
ord-808aaba49d1340bebee3bd7d1f7af931
Source dataset
uspto-grants-1979_02
Patent number
US04139559

Reaction notes

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