Hydrochloric Acid → HCID 17604238, compound

HRID 1882317Notes

Reaction equation

HRID 1882317 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][C:7]=1[O:14][CH3:15].[B-].[Na+].Cl>CO>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][C:7]=1[O:14][CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 882523methyl 2-(4-formyl-2-methoxyphenoxy)acetateHCID 22959485Vertellus

Product 1

HCID 17604238HCID 17604238, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-Formyl-2-methoxy-phenoxy)acetic acid methyl ester 71 (50 grams, 223 mmol) in methanol (500 mL) at 0° C. was added Sodium boro hydrate (4 grams, 106 mmol) in small portions, further stirred at 0° C. for 30 minutes and poured on to ice water (200 mL). The pH of mixture was adjusted to 2 with concentrated hydrochloric acid. Crude 72 was extracted into chloroform, dried over Na2SO4 and distilled to give 72 (40 grams, 62%) as a light yellow syrup.

Workup

  1. extractionCrude 72 was extracted into chloroform
  2. dry with materialdried over Na2SO4
  3. distillationdistilled

Sources & evidence

ORD record
ord-304dc680ef014e22894812c008c1776f
Source dataset
uspto-grants-2012_11
Patent number
US08318973B2

Reaction notes

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