Ammonia → [4-(2-Chloroethoxy)-2-(hydroxymethyl)-5-methoxyphenyl]methanol

HRID 2213796Notes

Reaction equation

HRID 2213796 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH2:15][CH2:16][Cl:17])=[CH:8][C:7]=1[CH2:18][O:19]C(=O)C)(=O)C.N>CO>[Cl:17][CH2:16][CH2:15][O:14][C:9]1[C:10]([O:12][CH3:13])=[CH:11][C:6]([CH2:5][OH:4])=[C:7]([CH2:18][OH:19])[CH:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 115879752-[(Acetyloxy)methyl]4-(2-chloroethoxy)-5-methoxybenzyl acetate

Product 1

HCID 11630152[4-(2-Chloroethoxy)-2-(hydroxymethyl)-5-methoxyphenyl]methanolYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 14.0 g of the 2-[(acetyloxy)methyl]4-(2-chloroethoxy)-5-methoxybenzyl acetate in 600 mL of methanol is stirred and cooled in an ice bath while ammonia gas is bubbled in, until the solution is saturated. The flask is stoppered and stored in the refrigerator for 15 hours. The reaction mixture is evaporated to give a white solid which is dried and chromatographed on a silica gel column eluting with 2:1 hexanes/ethyl acetate, to give 9.87 g of [4-(2-chloroethoxy)-2-(hydroxymethyl)-5-methoxyphenyl]methanol as a white solid, m.p. 934° C.

Workup

  1. customis bubbled in, until the solution
  2. customThe reaction mixture is evaporated
  3. customto give a white solid which
  4. customis dried
  5. customchromatographed on a silica gel column
  6. washeluting with 2:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-4f48d7fa4f6845aaadce20f6026fce85
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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