Hydrochloric Acid → HCID 21319729, compound

HRID 262021Notes

Reaction equation

HRID 262021 reaction equation
[ClH:1].[CH2:2]=[O:3].[CH3:4][C:5](O)([C:7]#[CH:8])[CH3:6].[CH2:10]([Cl:12])Cl>>[CH3:4][C:5]([CH:2]([O:3][CH:10]([Cl:12])[C:5]([CH3:6])([CH3:4])[C:7]#[CH:8])[Cl:1])([CH3:6])[C:7]#[CH:8]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6344DichloromethaneHCID 82582-Methyl-3-butyn-2-ol

Product 1

HCID 21319729HCID 21319729, compound

Procedure

Hydrogen chloride gas (80 grams, 2.2 moles) was bubbled into a mixture of paraformaldehyde (60.2 grams, 2.0 moles), and 2-methyl-3-butyn-2-ol (168.2 grams, 2.0 mole) in methylene chloride (500 ml.) over a 25 minute period, with constant stirring while maintaining the temperature between 2° C. to 8° C. Upon completion of the addition, the reaction temperature was allowed to rise to 10° C., then the lower organic phase separated, washed with ice water, separated and dried over anhydrous calcium chloride for 18 hours. The methylene chloride was removed by evaporation and the resulting liquid distilled at reduced pressure to give the chloromethyl ether, 1,1-dimethyl-2-propynylchloromethyl ether, 140 grams, 53%, boiling point 54° C. to 58° C./37 to 40 mm.

Workup

  1. temperaturewhile maintaining the temperature between 2° C. to 8° C
  2. additionUpon completion of the addition
  3. customto rise to 10° C.
  4. customthe lower organic phase separated
  5. washwashed with ice water
  6. customseparated
  7. dry with materialdried over anhydrous calcium chloride for 18 hours
  8. customThe methylene chloride was removed by evaporation
  9. distillationthe resulting liquid distilled at reduced pressure

Sources & evidence

ORD record
ord-3f4b359638cf46d6a51c0bb102ec0e27
Source dataset
uspto-grants-1979_05
Patent number
US04153448

Reaction notes

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