Ammonia → HCID 19767504, compound

HRID 1590597Notes

Reaction equation

HRID 1590597 reaction equation
C([O:8][CH2:9][C:10]([CH:15]1[CH2:18][CH2:17][CH2:16]1)([CH2:13][OH:14])[CH2:11][OH:12])C1C=CC=CC=1.N.[Na].[Cl-].[NH4+]>CCOCC>[CH:15]1([C:10]([CH2:9][OH:8])([CH2:11][OH:12])[CH2:13][OH:14])[CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 19767477HCID 19767477, compound

Product 1

HCID 19767504HCID 19767504, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 2-benzyloxymethyl-2-cyclobutylpropane-1,3-diol (49 g, 0.2 mol) in dry ether (200 ml) was added to liquid ammonia (450 ml) stirred at -70° C. Sodium pellets (14 g, 0.6 mol) were added and the stirred mixture was allowed to warm to -33° C. over 2 hours. Ammonium chloride (35 g, 0.65 mol) was added and the ammonia was allowed to evaporate overnight. The solid residue was extracted with ether, the extracts were combined, filtered and evaporated to leave 2-cyclobutyl-2-hydroxymethylpropane-1,3-diol as an oil (27.9 g, 87%) which was purified on a silica column eluting with chloroform then increasing amounts of chloroform:methanol (up to 9:1 v/v).

Workup

  1. additionwere added
  2. temperatureto warm to -33° C. over 2 hours
  3. customto evaporate overnight
  4. extractionThe solid residue was extracted with ether
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-630eea48975f4b48b683d285e1485955
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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