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Hydrochloric Acid → (2R)-3-(4-cyanophenoxy)propane-1,2-diol

HRID 466221
Notes
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Reaction equation

HRID 466221 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[CH2:4][O:3]1.Cl>CO.O>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C@H:5]([OH:6])[CH2:4][OH:3])=[CH:10][CH:11]=1)#[N:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15066863(4S)-2,2-Dimethyl-4-(4-cyanophenoxy)methyl-1,3-dioxolane

Product 1

HCID 12222186(2R)-3-(4-cyanophenoxy)propane-1,2-diolYield 72.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

77 g of (4S)-2,2-dimethyl-4-(4-cyanophenoxy)methyl-1,3-dioxolane, was dissolved in methanol (200 ml) and water (75 ml). Concentrated hydrochloric acid (0.5 ml) was added and the mixture was kept at 50° C. overnight. It was evaporated at reduced pressure and recrystallized from water to yield 46 g of the title compound as white leaves, m.p. 63°-65° C.

Workup

  1. customIt was evaporated at reduced pressure
  2. customrecrystallized from water

Sources & evidence

ORD record
ord-7edee3fdbde24096831ee3b4e44bbf59
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05155133

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes