Diphenyl Ether → HCID 53947048, compound

HRID 580953Notes

Reaction equation

HRID 580953 reaction equation
C([O:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:6]=1)C=C.[C:18]1(OC2C=CC=CC=2)[CH:23]=CC=C[CH:19]=1>>[CH2:23]([C:17]1[CH:16]=[C:8]([CH:7]=[CH:6][C:5]=1[OH:4])[O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:18]=[CH2:19]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 53873708Ethyl 4-allyloxyphenoxyacetate

Product 1

HCID 53947048HCID 53947048, compound

Procedure

A solution of ethyl 4-allyloxyphenoxyacetate (2.0 g) in diphenylether (15 ml) was heated at reflux for 12 minutes. The reaction mixture was allowed to cool to ambient temperature and the reaction mixture was poured onto a silica gel pad (Merck Art. No. 9385). Elution with hexane followed by a 4:1 (v/v) mixture of hexane and ethyl acetate gave ethyl 3-allyl-4-hydroxyphenoxyacetate (1.62 g) as a solid, mp 52.8° C.; microanalysis, found: C, 66.3; H, 7.20%; C13H16O4 requires: C, 66:1; H, 6.83%; NMR (CDCl3): 1.28 (3H, t), 3.35 (2H, d), 4.25 (2H, q), 4.55 (2H, s), 4.73 (1H, s), 5.07-5.20 (2H, m), 5.88-6.10 (1H, m) and 6.62-6.78 (3H, m); m/z 237 (M+H).

Workup

  1. temperatureat reflux for 12 minutes
  2. additionthe reaction mixture was poured onto a silica gel pad (Merck Art
  3. washElution with hexane
  4. additionfollowed by a 4:1 (v/v) mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-1af9ac7fb6594b9784dd001d31da4194
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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