Hydrochloric Acid → {3-Chloro-4,5-bis[(prop-2-yn-1-yl)oxy]phenyl}methanol

HRID 1708982Notes

Reaction equation

HRID 1708982 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:14][CH2:15][C:16]#[CH:17])[C:9]=1[O:10][CH2:11][C:12]#[CH:13])[CH:5]=[O:6].[BH4-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:14][CH2:15][C:16]#[CH:17])[C:9]=1[O:10][CH2:11][C:12]#[CH:13])[CH2:5][OH:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 141303053-Chloro-4,5-dipropargyloxybenzaldehyde

Product 1

HCID 14130328{3-Chloro-4,5-bis[(prop-2-yn-1-yl)oxy]phenyl}methanolYield 105.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chloro-4,5-dipropargyloxybenzaldehyde (14.7 g) was added to a solution of sodium borohydride (3.6 g) in ethanol (150 ml) at a temperature below 30° C. After stirring at room temperature for 2 hours, the resultant mixture was poured into dilute hydrochloric acid under cooling and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 3-chloro-4,5-dipropargyloxybenzyl alcohol (15.60 g). nD17.0 1.5713.

Workup

  1. temperatureunder cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f828332c5964b83aea06e86cbbbe16e
Source dataset
uspto-grants-1990_08
Patent number
US04946865

Reaction notes

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