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

HRID 989351Notes

Reaction equation

HRID 989351 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. 93-4° 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-2435bf0aa8e14334b7e4dbdbef0b31b4
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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