4-[(4-Methoxyphenyl)methoxy]-3-(phenylmethoxy)benzaldehyde → 3-Benzyloxy-4-hydroxybenzaldehyde

HRID 2213566Notes

Reaction equation

HRID 2213566 reaction equation
COC1C=CC(C[O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=2[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=CC=1>C(O)(=O)C>[OH:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][C:12]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 1

HCID 219575084-[(4-Methoxyphenyl)methoxy]-3-(phenylmethoxy)benzaldehyde

Product 1

HCID 110206353-Benzyloxy-4-hydroxybenzaldehydeYield 82.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-[(4-Methoxyphenyl)methoxy]-3-(phenylmethoxy)benzaldehyde (25.93 g, 0.074 mol) in acetic acid (200 mL) was heated to reflux (150□C) and stirred for 2 days. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (200 mL). The organic solution was washed with water (200 mL) and 0.5M aqueous sodium hydroxide (5×200 mL). The basic extracts were combined, acidified to pH 1 with concentrated HCl and back extracted with ethyl acetate (2×300 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to a gummy solid, which was recrystallized from ethyl acetate and petroleum ether to give the product as a pale brown powder (14 g, 82%). 1H NMR (CDCl3) δ 9.84 (s, 1H, O═C—H), 6.26 (1H, s, OH), 5.20 (s, 2H, CH2Ph).

Workup

  1. temperatureto reflux (150□C)
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate (200 mL)
  4. washThe organic solution was washed with water (200 mL) and 0.5M aqueous sodium hydroxide (5×200 mL)
  5. extractionback extracted with ethyl acetate (2×300 mL)
  6. dry with materialThe organic solution was dried over sodium sulfate
  7. customevaporated in vacuo to a gummy solid, which
  8. customwas recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-7d54279ed93848c582aa0e7a6c9ae415
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

Loading…